FOR LIFE SCIENCE RESEARCH Volume 2 Number 6
Carbohydrate Metabolism and PPAR Signaling
■ Introduction
■ Glycolysis
■ Pyruvate Transformations
Innovative products for metabolomic ■ Citric Acid Cycle research and biomarker discovery help you navigate the life science pathways. ■ Monosaccharide Biosynthesis
■ Pentose Phosphate Pathway
■ Calvin Cycle
■ PPAR Signaling Enzyme Explorer Metabolic Pathways Resource Center
The evolutionary pathway of life science technology has brought today's researchers full circle to a destination we now call metabolomics.
The Sigma Enzyme Explorer Metabolic Pathway Resource Center provides the online tools you need to explore the metabolome.
In 1947 Sigma produced the first batch of commercially available ATP. Since then, Sigma has consistently expanded its product offerings to what is now the most comprehensive line of organic metabolites, enzymes and analytical tools in the world. The cornerstone of our commitment to metabolomics is our long-standing alliance with the IUBMB to produce animate and publish the Nicholson Metabolic Pathway Charts.
To take advantage of these and many other free resources visit the Sigma metabolomics resource at sigma.com/metpath
sigma.com 1
Introduction The analysis and understanding of the functional biology of cells, tissues and organisms not only require information on the genome and proteome level, but also a snapshot of the small molecules present. Low-molecular weight metabolites have FOR LIFE SCIENCE RESEARCH been the subject of classical biochemical research in the 20th century and have been further defined as substrates and products of enzyme reactions. Changes in the levels 2007 of specific metabolites are used in routine analysis of healthy and pathological states of humans and animals. In addition, microbial and plant systems used in biochemical Volume 2 manufacturing benefit from the quantification of metabolites (e.g. D(+)-glucose, Number 6 acetate and L(+)-lactate). Advances in separation and detection technologies along with the availability of new metabolite standards have improved the ability to analyze defined target molecules. Table of Contents Analysis of large numbers of related metabolites up to the complete metabolome have now become possible. Carbohydrate Metabolism and A rapid global analysis can be used as a metabolic fingerprint for phenotype or sample classification. On a more detailed level, the analysis of specific metabolic pathways and PPAR Signaling changes under experimental conditions can be utilized as a metabolic profile while also contributing information to genomic and proteomic studies. Sigma offers hundreds of metabolite standards. This issue of BioFiles features products related to carbohydrate metabolism. Introduction ...... 1
Cationic and Anionic Metabolites ...... 2
Glycolysis ...... 4
Pyruvate Transformations ...... 10
Citric Acid Cycle...... 16
Monosaccharide Biosynthesis ...... 21
Pentose Phosphate Pathway ...... 25
Calvin Cycle ...... 27
PPAR Signaling ...... 29
To order a 33 in. x 50 in. Metabolic Pathways Poster, click here. Cationic Metabolites of Increasing Mass/Charge-Ratios 2 sigma.com metabolites arrangedintheorder ofincreasing molecularweight/chargeare shownin As thediscoveryofnovelmetabolitesissupportedbycomparisonwithexistingmetabolites,alistbothcationicandanionic Cationic MetabolitesofIncreasing Mass/Charge-Ratios uie11P1655 12072 121 121 Purine Benzamidine N-Methyl- N,N-Dimethylglycine GABA a-Aminoisobutyrate Cadaverine Hexylamine a-Aminocyclopropane-1-carboxylate Succinimide 1-Methyl-2-pyrrolidone 4-Hydroxymethylimidazole 2-Hydroxypyridine Aniline 3-Amino-1,2-propanediol Sarcosine 2-Aminoimidazole b-Guanidinopropionate e-Amino-n-caproate d-Aminolevulinate beta-Phenylethylamine Benzamide N,N-Dimethylaniline Benzimidazole Guanidinoacetate Pyridine Cysteamine Isopropanolamine Adenine Imidazole-4-acetate 5-Methylcytosine 1-Methylhistamine Taurine a-Methyl- Dihydrouracil Creatinine Uracil Cytosine 4-Aminophenol Hypotaurine Diethanolamine 1,4-Butanediamine Piperazine Piperidine 3-Amino-1,2,4-triazole Pyrimidine Glycyl-glycine 5-Aminoindole 4-Aminoindole L D L L L L L L L L L L L L L DL L L L 1,3-Diamonipropane Methylguanidine 3-Aminopr Urea Cationic MetaboliteStandards 1 Table Creatine N-Acetylputrescine 1,1-Dimethyl biguanide 1-Amino-1-cyclopentanecarboxylate Cyanurate Oxoproline Octylamine Isoguvacine -Aspartic acid -Asparagine -Ornithine -Norleucine -Hydroxyproline -Leucine -Isoleucine -Cystein -Threonine -Homoserine -Norvaline -Valine -Proline -Serine -Alanine -b-Alanine -Glycine -Ornithine -2,3-Diaminopropionate DL L -alanine opionitrile -serine m/z 100 115 104 105 104 103 102 100 134 134 133 133 132 132 132 122 122 122 120 119 118 118 118 116 106 130 136 127 126 126 126 114 113 112 110 106 133 133 133 2 M6877 120 104 104 102 132 132 132 132 122 120 132 131 130 130 130 130 128 110 133 85 71 99 96 94 92 90 90 76 80 78 76 89 87 86 81 75 74 90 61 H5,680-0 A4,810-5 D2,360-2 21,970-3 Cat. No. M9768 M6751 M4910 M0377 O4386 G7403 O5250 G6878 G7278 D7628 A8056 A3134 D1502 D1156 C1541 H1877 A9880 A7627 A8949 A0884 N6877 H5534 N7627 A1531 A8626 C4255 U0750 C3506 H1384 D0681 A5835 A8504 A3903 A2504 A3785 H6515 A7752 C3630 A8784 D5035 U0631 V0500 78769 39430 30089 12250 50920 80621 83120 B2009 28640 83170 74988 S9381 S7672 P2641 T8625 P0380 S4500 P4036 T0625 P7630 P5881 G-002 L8912 I0375 I2752 2676 9265 8225 8245 8244 9160 Piperacillin Leupeptin Leucyl-leucyl-tyrosin Gramine gamma-Guanidinobutyrate Spermidine 4-Methyl-5-thiazoleethanol Tropine 6-Hydroxynicotinate Urocanate para-Aminobenzoate Anthranilate 3,4-Dihydroxyphenethylamine 1-Adamantanamine Guanine Triethanolamine 3-Methyladenine 2,6-Dimethylaniline O-acetyl- Acetylcholine Porphobilinogen o-Phenanthroline Fusarate N-Ethyl- Pterin Nicotine 3-Indole ethanol Tolazoline Allantoin 3-Indolylacetonitrile Isatin Carbachole N-Acetylspermine 2’-Deoxyuridine N-Acetyl- Harmaline Baclofen Minoxidil Spermine DOPA Caffeine 2,6-Diaminoheptanedioate Castanospermine Quisqualate Pyridoxine Mecamylamine Pyridoxal Phenylephrine L D L L L DL Cationic MetaboliteStandards L L L L L L L L L L Tyramine Pralidoxime Hypoxanthine N-Acetyl- S-Adenosyl- Glutathione Nopaline Guanosine Eserine Inosine Adenosine Octopine Uridine Cytidine Thymidine -Methionine -Glutamic acid -Glutamine -Lysine -Homocarnosine -Carnosine -Cystathionine -Tryptophan -Tyrosine -Citrulline -Arginine -Phenylalanine -Carnitine -Histidine -Penicillamine -Homocysteine L -Glutamine L D L -serine -Ornithine (+)-glucosamine L -homocystein Table 1 Table and Table 2 Table . m/z 144 150 427 146 146 142 140 139 138 138 385 175 148 154 150 150 147 150 148 147 146 227 181 180 164 163 162 161 159 147 227 223 222 205 182 176 175 166 162 156 235 229 215 214 210 203 195 191 190 190 170 168 168 518 408 175 138 137 137 136 175 152 152 151 157 148 308 305 284 276 269 268 247 245 244 243 241 198 168
G1,080-6 Cat. No. A 6625 M9281 M9625 M4145 M9020 G6503 G1251 G3126 Q2128 G6779 G6529 G6752 O4875 U7500 A9878 A1506 A9384 A3626 A6262 H8502 N0267 A7878 C4382 C9625 C7505 A8625 C7629 A5006 C0158 H8000 D5412 H2256 C8960 D1377 C3784 H9377 H4628 N6134 A9251 U3750 C3506 H4885 D9503 54405 36766 55968 54350 B5399 85590 57280 58240 S2626 T7878 P4875 P1134 P9375 P1132 T6886 T0254 T3754 P2126 P5669 P9130 P6126 P8396 T7255 P9053 E4393 T9534 E8375 T9250 L2884 L5501 F6513 L9890 I1024 1467 6649 Anionic Metabolites of Increasing Mass/Charge-Ratios 3
sigma.com I0879 I1017 F6625 F8399 F3627 P5397 S1129 T0251 T9375 I 4375 I 2879 T7004 T6754 P6888 S2625 T5875 P3161 P9255 E0377 T8260 79535 R7750 R9875 82890 B1268 X1000 X3250 N6522 N8129 N0505 N8129 C3144 A2056 D4635 D4001 C1506 U6625 D6500 D0758 A7699 D4010 U4625 U6751 C8271 D7250 C9755 U4125 D6000 A2754 D9250 A5028 U5252 A5763 A1651 D7006 D9625 A1752 D6250 D0126 U6375 A4137 C1131 D7783 D3876 A2388 D7625 C8631 D5764 A5707 H7254 D3126 G5884 G7127 G8377 G7504 F 0752 G7879 G7000 G8645 G5509 G4500 M4263 M4778 Cat. No. 662 664 742 744 766 784 808 822 852 866 466 467 481 482 483 490 491 506 506 507 522 565 579 614 363 386 401 402 403 410 426 426 427 442 455 462 607 362 389 426 426 443 346 347 346 344 331 330 339 323 328 322 329 321 307 308 306 303 304 259 265 275 289 259 202 193 258 259 195 201 204 205 209 218 229 229 246 247 194 199 207 208 213 m/z -6,8-Thioctate amide -6,8-Thioctate reduced -Glucuronate -Glucosamine-6-phosphate NAD NADH NADP NADPH CoA FAD AcetylCoA PropionylCoA MalonylCoA SuccinylCoA dCTP CMP-N-acetylneuramate dUTP TTP CTP UTP dATP dITP ATP dGTP ITP GTP UDP-glucose UDP-glucuronate UDP-N-acetylgalactosamin dGDP IDP FMN dCDP Ribose-1,5-diphosphate TDP CDP UDP dADP ADP Adenosine-3’,5’-diphosphate Adenosine-5’-phosphosulfate GDP 7,8-Dihydrofolate Adenylosuccinate XMP IMP GMP dGMP AMP dIMP Fructose-1,6-diphosphate cGMP dAMP cAMP quinone Pyrroloquinoline UMP TMP CMP N-Acetylneuramate dUMP 2,3-Diphosphoglycerate Gluconate-6-phosphate Argininosuccinate cTMP cCMP dCMP Glucose-6-phosphate Fructose-6-phosphate Glucose-1-phosphate Ribulose-5-phosphate Pyridoxal-5’-phosphate Pyridoxamine-5’-phosphate Anionic Metabolite Standards Anionic Metabolite D DL DL D O-Hydroxyhippurate Gluconate Erythrose-4-phosphate Sebacate Indole-3-pyruvate Xanthurenate N-Benzyloxycarbonylglycine Mucin Pantothenate 2-Deoxyribose-5-phosphate Ribose-5-phosphate 1730 1160 I1137 F2752 L6402 S3674 P8574 P0503 P0257 T0632 S5922 P8877 S5375 P5671 T1807 P0878 B7521 68253 21873 49660 59950 64280 11470 58790 71900 54610 81860 89902 89890 22560 V9759 K8875 K0629 K1750 H6501 C4026 N4126 H4377 C3750 C2875 A7426 A0262 A6037 D8132 A5960 C7630 A3412 H3766 A3258 C0706 C7757 H5005 D7137 G8766 G6002 G4627 G8284 G7528 G2138 M4795 M2422 M6126 M6413 Cat. No. T3,520-3 13,104-0 12,954-2 40,292-3 40,290-7 C8,085-7 C8,260-4 M5,405-8 B10,350-0 99 95 87 87 89 93 73 73 75 91 71 69 122 101 103103 103 105 54913/06367 114 115 115 116 117 117 121 122 101 115 149 151 129 131 131 101 147 129 129 143 145 146 129 187 140 185 191 173 124 137 137 139 124 185 179 173 175 173 168 168 173 135 137 123 133 135 184 188 190 191 178 179 171 172 169 m/z -cysteine L nate 152 C4418 -serine L -glutamate -methionine L L -Isocitrate D -Aconitate -Cysteate -Cysteine sulfi -Malate (+)-Tartrate Pentanoate b-Hydroxypyruvate b-Hydroxybutyrate Malonate Glycerate Maleamate Hexanoate Fumarate 3-Methyl-2-oxobutanoate Guanidoacetate Methylmalonate Succinate Benzoate Isonicotinate Nicotinate p-Hydroxyphenylacetate Isovalerate 2-Oxobutyrate 4-Carboxybenzaldehyde Mesaconate 4-Methyl-2-oxovalerate Glutarate propionate 3-Ureido Tiglate threo-beta-Methyl-aspartate trans.Cinnamate Itaconate Methanesulfonate Caprylate 2-Oxoglutarate Citraconate N-Acetyl- Azelaate Butyrate Pyruvate Lactate Chloroacetate Thioglycolate Ethanolamine phosphate (S)-(+)-1-Aminoethylphosphonate 2-Phosphoglycerate Propionate Glycolate Acrylate Dehydroascorbate (-)-Shikimate Phenylphosphate m-Hydroxybenzoate Salicylate Acetylphosphate 2,5-DihydroxybenzoateProtocatechuateDihydroorotateAcetylcysteinep-Coumarateo-Coumaratebeta-Phenylpyruvate3,4-DihydroxyphenylacetatePhosphoenolpyruvate 153 153 157 G5254 167 162 163 163 163 167 P5630 D7003 D9128 A8199 P8001 C9008 C4400 P7127 2-Aminoethylphosphonate 3-Phosphoglycerate Threo- Glucose O-Phospho- p-Hydroxyphenylpyruvate L L L L Anionic Metabolite Standards Anionic Metabolite Table 2. Table Propiolate Glyoxylate Ascorbate S-Carboxymethyl- Glycerol-3-phosphate 2-Quinolinecarboxylate cis Glyphosate phosphate Dihydroxyacetone m-Toluate p-Hydroxybenzoate p-Toluate Citrate N-Acetyl- Anionic Metabolites of Increasing Mass/Charge-Ratios Increasing of Metabolites Anionic Glycolysis 4 sigma.com retro-aldol reaction into reaction offructose-1,6-bisphosphate(4),whichiscleavedina A keybranchingreaction isthefourthreaction: aring-opening phosphate (4). fructose-6-phosphate (3)isconvertedtofructose-1,6-bis- The third reaction isanotherphosphorylationwithATP, whereby subsequent keto-enol-tautomerization. reaction tofructose-6-phosphate(3)occursviaring-openingand The isomerizationofglucose-6-phosphate(2)inthesecond in thefirstreaction withATP togiveglucose-6-phosphate(2). Figure 1. way asillustratedin term requirements andbeginswiththeEmbden-Meyerhoff-Path- The catabolismofglucoseistheprimaryenergysource forshort- such asstarch to carbohydrates are enzymaticallyhydrolyzed tomonosaccharides, main storagemoleculesofsolarenergy. Wheningested,complex Carbohydrates synthesizedduringphotosynthesisactasthe Glycolysis dihydroxyacetone phosphate(6). Embden-Meyerhoff-Pathway. D (+)-glucose. Figure 1. D HO -glyceraldehyde-3-phosphate (5),and HO OH 23 12
D H (+)-Glucose (1)isphosphorylated OH O 3 C OH O 11 O ONa NaO P ONa HO O OH OH O OH NaO H O 2 C P 10 ONa O O NaO ONa NaO dehydration reaction from 2-phospho- The nextmetabolitephosphoenolpyruvate(10)isformedina The eighthreaction isanisomerizationof3-phospho- 3-phospho- seventh reaction from thecarboxylgroup of(7)toADPgive This phosphategroup inthe1-positionistransferred inthe 1,3-bisphospho- carboxylic acidandthenphosphorylatedinthe1-positiontoyield aldehyde-3-phosphate from bothroutes isoxidizedattheC1toa Nicholson-IUBMB animationofglycolysisat theSigmaMetabolomicsResourceVisit Centertoview the giving ATP andpyruvate(11). phosphate group from phosphoenolpyruvate(10)toADP, thereby pyruvate (11)isconcludedbythetenthreaction, whichtransfersa The glycolysispathwayfrom reaction. (8) to2-phospho- by anisomerization.Inthesixthreaction thecombined back into The branchviadihydroxyacetonephosphate (6)ischannelled O P O P ONa O NaO NaO ONa NaO NaO O NaO NaO OH P P OH D HO O O O -glyceraldehyde-3-phosphate (5)inthefifthreaction P O O D HO 7 O 9 8 O -glycerate (8). HO O 5 NaO OH 4 OH O OH D O -glycerate (7). D OH OH O O O P O -glycerate (9). OH O P O ONa ONa ONa O ONa O ONa H P ONa ONa OO HO D (+)-glucose (1)totwomoleculesof O 6 NaO D -glycerate intheninth P sigma.com/metpath D -glycerate D -glycer- . Glycolysis 5
sigma.com 1 g 5 g 1 g 1 g 5 g 1 g 1 g 5 g 10 mg 25 mg 10 mg 100 mg 250 mg 500 mg 250 mg 500 mg 100 mg 500 mg phos- EC No. 2475054 2475054 EC No. 0.05 mol % ≤ 50× 4-200R is also 1.5 mol % ® ≤ EC No. 3009865 EC No. [26177-86-6] phate barium salt [81028-91-3] phate solution salt barium phate diethyl acetal phate; Harden-Young ester; Hexose di phate; Harden-Young [103213-47-4] [93965-35-6] phate trisodium salt 100 µg/mL diol 1-phos phos O [591-59-3] 2 ≤ B phate dipotassium phate dipotassium salt phate hydrate disodium salt phos O FW 304.10 (Anh) (Anh) 304.10 O FW 2 hyde 3-phos hyde 3-phos ose 1,6-di FW 406.06 FW 3 P · xH FW 336.32 336.32 FW alde alde Na 9 2 P FW 379.49 379.49 P FW 2 furan 7 O P B B B B 2 PK cer cer 12 P FW 170.06 170.06 P FW 9 6 O BaO O Na O 11 7 15 11 11 -Gly -Gly H H H H H 45-55 mg/mL in H ≥98% (TLC) ~98% (enzymatic) ~98% (enzymatic) F6803-10MG F6803-1G F6803-5G G5251-25MG G5251-100MG G5251-250MG G5251-500MG G5251-1G G5376-250MG G5376-1G F1502-500MG F1502-1G F3627-10MG F3627-100MG F3627-500MG F3627-1G F3627-5G G5376-5G 6 3 7 6 6 -Fructose 1,6-bis -Fructose 6-phos -Fructose 6-phos -Fructose 6-phos (+)Fructo included for preparing a solution of glyceraldehyde 3-phosphate included for preparing this derivative at no extra charge. Instructions for preparing from this derivative accompanies each package. this solution from fructose 1,6-diphosphate...... C D at: store C Ba...... at: ship: dry ice store 3,3-Diethoxy-1,2-propane A package of specially washed Dowex at: store D C glucose 6-phosphate...... at: store D C BRN 5686786 mol % glucose 6-phosphate...... <1.5 mol % fructose 1,6-diphosphate...... <0.05 at: store DL DL D phate C 5 g 1 g 5 g 1 g 5 g 10 g inquire 100 mL 500 mL 250 mg phos- EC No. 2537780 2537780 EC No. EC No. 2269068 EC No. ≥98.0% (enzymatic) EC No. 2589210 EC No. EC No. 2048243 BRN 506211 2048243 BRN EC No. [38099-82-0] [103213-44-1] [5541-93-5] O phate trisodium salt 2 pionic acid phate; Harden-Young ester; Hexose di phate; Harden-Young [127-17-3] pro pro [54010-71-8] phate tetra(cyclohexylammonium) salt phate octahydrate trisodium phate octahydrate salt phos phate sodium salt ; G-6-P Na; Robison ester sodium salt ; G-6-P phate phos B phos phos phate sodium salt O FW 550.18 O FW N FW 736.81 N FW 2 enolpyruvate heptahydrate ≥97.0% (enzymatic) ≥98.0% (NT) 13 O FW 360.09 360.09 O FW 2 , crystallized, anhydrous, , crystallized, anhydrous, , , H ose 6-phos 6 ose 1,6-di pho · 8H 2 P -Fructose 1,6-di ≥98.0% (T) · 4C D P FW 282.12 282.12 P FW P · 7H 12 pyran pionic acid; 2-Oxo 2 furan 9 6 O P E B E E O 3 H; 3 12 3 pho(enol)pyruvic acid heptahydrate trisodium salt O NaO Na Na R: 34 S: 26-36/37/39-45 EC No. 204-824-3 FP: 82 °C (180 °F) °C (180 R: 34 S: 26-36/37/39-45 EC No. 204-824-3 FP: 82 14 12 2 COCOOH FW 88.06 COCOOH FW 11 odium phos 3 H H H H ≥95% BioChemika BioChemika purum, BioChemika F0752-5G F0752-10G 49282-250MG 49282-1G 79435 47810-5G 15940-100ML 15940-500ML 49282-5G 47810-1G -Keto pro pro -Keto 6 6 3 6 -Fructose 1,6-bis -Glucose 6-phos -Fructose 1,6-bis -Fructose 1,6-bis (+)Fructo (+)-Gluco BRN 5787568 C Hexose monophosphates...... essentially free at: store Hygroscopic Substrate for the determination of glucose-6-phosphate EC 1.1.1.491 dehydrogenase, 10 in H [α]20/D +34±1°, c = D store at: store D D at: store Phos Tris C BRN 4611329 D M Pyruvic acid α water...... ~25% at: store D FDP-Na Non-Labeled Metabolites for Metabolites Non-Labeled Glycolysis store at: store C BRN 3837985 CH phate C Glycolysis 6 sigma.com C C A 1M/260, H A 1M/260, sulfate (SO solubility [α]20/D +53±2°,3 hr, c= 10 inH H [α]20/546 +62±2°,3 hr, c= 10 inH C Dextrose D store at: usually 2-4H D D store at: usually 2-4H C G-6-P-Na D store at: D D Cr...... <0.0005% Co...... <0.0005% Cd...... <0.0005% Ca...... <0.001% Bi...... <0.0005% Ba...... <0.0005% As...... <0.0001% Al...... <0.0005% chloride (Cl ign. residue...... <0.1% (asSO4) LOD...... <0.1% Insoluble matter...... passesfiltertest ...... H A 1M/280, (+)-Gluco (+)-Gluco -Glucose 6-phos -Glucose 6-phos -(+)-Glucose -Glucose 6-phos 6 6 6 6 G7528-5KG G7528-1KG G7528-250G G7528-10MG G7375-5G G7375-1G G7250-25G G7250-5G G7250-1G G7250-500MG G7250-10MG G6526-5G G6526-1G SigmaUltra, 99.5%(GC) Sigma Grade,98-100% Sigma Grade,98-100% ≥95% H H H H 2 O...... 1 M at 20 °C, clear,at 20°C, O...... 1 M colorless 11 11 12 12 O K Na O 2 9 6 O PK FW 298.23 FW 180.16 2 B B B 2 O 9 P ·xH pyran pyran 9 4 P ·xH - 2- )...... <0.005% )...... <0.005% 2 2 O...... <0.02 O...... <0.02 2 2 O/mole O/mole ose 6-phos ose 6-phos 2 O FW 336.32 (Anh) 2 O FW 304.10 (Anh) phate hydrate disodium salt phate hydratedisodium salt phate potassium phate hydrate dipotassium salt phate hydratedipotassium [50-99-7] phate dipotassium salt phate dipotassium salt phate potassium [103192-55-8] ECNo. 2077578 BRN 1724615 2 O (lit.) Zn...... <0.0005% Sr...... <0.0005% Pb...... <0.0005% Ni...... <0.0005% Na...... <0.005% Mo...... <0.0005% Mn...... <0.0005% Mg...... <0.0005% Li...... <0.0005% K...... <0.005% Fe...... <0.0005% Cu...... <0.0005% 2 [3671-99-6] O (lit.) BRN 5199009 500 mg 10 mg 10 mg 250 g 25 g 5 kg 1 kg 5 g 1 g 5 g 1 g 5 g 1 g BRN 4771585 C C enoic acid monopotassium salt;mono-Potas Mono-potas Phos store at: C D store at: Mono-sodium phos Phos store at: (−)-Disodium D- store at: C D ECNo.224-247-0store at: C acid monopotassium salt; mono-Sodiumphos (−)3-Phos pho gly (−)3-Phos pho gly 3 3 3 3 3 P0769 P0564-1G P0564-250MG P0564-100MG P8877-5G P8877-1G P8877-10MG P8627 P7127-5G P7127-1G P7127-500MG P7127-250MG P7127-100MG (−)-3-Phos pho gly ~95% ~95% ≥97% (enzymatic) ~95% ≥97% (enzymatic) H H H H H 4 4 4 5 5 KO O NaO Na O pho(enol)pyruvic acid monopotassium salt salt acid hydratemonosodium pho(enol)pyruvic 7 7 PNa PBa FW 321.37 2 6 O P FW 206.13 B B B B 6 P ·H 7 P FW 230.02 3 FW 252.00 sium phos D -3-phos pho 2 O FW 208.04 pho ceric acid trisodium salt ceric acid barium salt pho ceric acid disodium salt enolpyruvate; 2-(Phos [4265-07-0] enolpyruvate; PEP-K; 2-(Phos enolpyruvate; PEP-K; gly cer ate; [80731-10-8] [86879-11-0] B [6134-04-9] [53823-68-0] D -Gly cer ECNo. 2242470 BRN 4603446 BRN 3767836 sium phos phono oxy)-2-prop ate 3-phos pho ECNo. 2588107 enolpyruvate monohydrate pho phono phate disodium salt phate disodium enolpyruvate oxy)-2-prop- enoic P0769 1 P8627 1 250 mg 100 mg 500 mg 250 mg 100 mg 10 mg 1 g 5 g 1 g 5 g 1 g Glycolysis 7
sigma.com 1 g 1 g 100 mg 250 mg 250 mg 100 mg 500 mg 250 mg 100 mg 500 mg OH) OH) OH) OH) OH) 4 4 4 4 4 [30737-83-8] BRN 5810734 BRN [106032-61-5] O (trace NH O (trace NH O (trace NH O (trace NH O (trace NH 2 2 2 2 2 [138079-87-5] [287100-67-8] [106032-62-6] 2 2 C C C C C 13 13 C 1 1 2 2 13 13 13 CDO FW 181.16 CDO FW CDOHCHO FW 181.16 181.16 FW CDOHCHO 13 C C 4 3 13 13 C 1 1 FW 182.14 FW 182.14 FW 6 6 FW 181.15 181.15 FW 13 6 O O O 12 12 12 [CHOH] [CHOH] H H 2 2 4 4 H 5 C C 2 2 99 atom % 98 atom % 98 atom % D 99 atom % 98 atom % D 453196-100MG 453196-250MG 310816-250MG 310816-1G 453188-100MG 453188-500MG 310824-250MG 310824-1G 310808-100MG 310808-500MG C C CC -Glucose-1,2- -Glucose-1,6- -Glucose-2-d -Glucose-6- -Glucose-1-d ]25/D +52.0°, c = 2 in H c = [α]25/D +52.0°, mol wt 182.12 by atom % calculation mol wt 182.12 by atom % calculation mol wt 181.14 by atom % calculation HOCH Hygroscopic Dextrose-1,2- D Dextrose-1,6- Hygroscopic D Dextrose-2-d HOCH Hygroscopic D Dextrose-6- 13 2 in H [α]25/D +52.0°, c = D Dextrose-1-d D 13 13 mol wt 181.16 by atom % calculation % calculation mol wt 181.16 by atom 2 in H [α]25/D +52.0°, c = ]25/D +52.0°, c = 2 in H [α]25/D +52.0°, c = 2 in H [α]25/D +52.0°, c = 1 g 1 g 1 g 2 g 3 g 1 g 10 g 10 g 250 mg 250 mg 100 mg 250 mg 100 mg 500 mg OH) OH) 4 4 OH) 4 BRN 2263682 BRN O (trace NH O (trace NH 2 2 C O (trace NH 2 13 [105931-74-6] [40762-22-9] [18991-62-3] [110187-42-3] 2 C C C C C 13 13 13 6 -Glucose-ul- 13 13 D 2 C ; C C 13 6 FW 181.15 FW FW 181.15 FW 13 13 C 6 6 FW 182.17 182.17 FW FW 186.11 FW 6 13 6 O O O O 12 12 10 H H 12 5 5 H H 2 6 D 98 atom % D 99 atom % 99 atom % 99 atom % 310794-250MG 310794-1G 297046-250MG 297046-1G 389374-100MG 389374-250MG 389374-1G 389374-2G 389374-3G 389374-10G 297046-10G 282650-100MG 282650-500MG 282650-1G CC CC C 6 -Glucose-2- -Glucose-1- -Glucose- -Glucose-6,6-d ]25/D +52.0, c = 2 in H [α]25/D +52.0, c = ]25/D +52.0, c = 2 in water + trace NH4OH 2 in water + trace [α]25/D +52.0, c = % calculation mol wt 182.15 by atom mol wt 181.14 by atom % calculation mol wt 181.14 by atom % calculation mol wt 186.05 by atom % calculation 13 Dextrose-2- ]25/D +52.0°, c = 2 in H [α]25/D +52.0°, c = Dextrose-1- 13 D Hygroscopic Dextrose- 13 Hygroscopic Hygroscopic D D D Dextrose-6,6-d C Stable Isotope-labeled Metabolites Metabolites Isotope-labeled Stable for Glycolysis ]25/D +52.0°, c = 2 in H [α]25/D +52.0°, c = Glycolysis 8 sigma.com CH CH 13 Hygroscopic Dextrose- D CH Pyruvic acid-1,2- Sodium pyruvate-1,2- 13 Pyruvic acid-3- Sodium pyruvate-3- Pyruvic acid-2- Sodium pyruvate-2- 13 Pyruvic acid- Sodium pyruvate- Moisture sensitive Pyruvic acid-1- Sodium pyruvate-1- 13 Pyruvic acid-2,3- Sodium pyruvate-2,3- mol wt192.88byatom%calculation mol wt112.01byatom%calculation mol wt111.03byatom%calculation mol wt111.03byatom%calculation mol wt112.99byatom%calculation mol wt111.03byatom%calculation mol wt112.01byatom%calculation [α]25/D +52.0°,c= 2 inH -Glucose- C CH CH CH 552151-5G 552151-1G 552151-500MG 493392-500MG 490733-250MG 490725-500MG 490717-500MG 490709-250MG 486191-500MG 99 atom % 99 atom % 99 atom 99 atom % 99 atom 99 atom % 99 atom 99 atom % 99 atom % 99 atom % 99 atom 3 3 3 6 13 13 CO H 3 3 3 13 13 5 CO COCO COCO D 13 CO COCO 7 13 CO O 13 6 CO 13 C FW 193.15 2 2 2 13 CO 6 13 Na FW 111.04 Na FW 111.04 Na FW 111.04 ,C-d 2 2 C 13 13 13 C Na FW 112.03 Na FW 112.03 2 3 C sodium salt C sodium salt C sodium salt C sodium 6 13 13 Na FW 113.02 sodium salt sodium 13 13 13 13 13 13 13 ,C-d 7 C C C; 97-99 atom % D C C C C C C ; 2 2 D sodium salt sodium sodium salt sodium -Glucose- 7 13 C 13 13 13 3 C C C [201417-01-8] 13 13 C C 2 2 2 13 O (traceNH C [124052-04-6] [87976-70-3] [87976-71-4] 6 [312623-97-5] [89196-78-1] ,1,2,3,4,5,6,6-d [142014-11-7] 4 OH) 7 500 mg 500 mg 250 mg 500 mg 500 mg 250 mg 500 mg 5 g 1 g mol wt192.11byatom%calculation 13 Pyruvic acid-3- Sodium pyruvate-3- [α]25/D +52.0°,c= 2 inH 13 Dextrose-3- D 13 Phos 13 Pyruvic acid- Sodium pyruvate- M 13 Pyruvic-1- Pyruvic-1- Hygroscopic [α]25/D +52.0°,c= 2 inH C Dextrose-d D Hygroscopic mol wt112.54byatom%calculation mol wt181.14byatom%calculation mol wt207.12byatom%calculation S&P tested Hygroscopic -Glucose-3- -Glucose-d 6 CD CC CC CH CC 605409 571237-50MG 660957 677175 616338-250MG 608483-1G 99 atom % 99 atom 97-99 atom % D 97-99 atom 99 atom % 99 atom 99 atom % 99 atom % 99 atom 95% (CP),99 atom % D 12 R:34S:26-36/37/39-45FP:82 °C (180 °F) 3 5 2 3 2 COCO H H H O 13 pho(enol)pyruvic acid-3- 12 4 4 6 CO KO O FW 192.23 O 13 3 6 13 FW 89.05 12 6 C acid(free acid) 13 FW 181.15 P FW 207.13 2 13 13 CO Na FW 114.06 C C acid(free acid) C 13 12 13 2 3 C,d Na FW 113.02 sodium salt sodium 13 13 13 13 C C; 50-60 atom % D C C C 3 sodium salt sodium 13 C 13 3 C,d 13 2 2 3 O (traceNH O (traceNH C 13 [142014-11-7] C potassium salt C potassium N 4 4 OH) OH)
N 250 mg inquire inquire inquire 50 mg 1 g Glycolysis 9
sigma.com 1 µCi 50 µCi 50 µCi 100 µCi 250 µCi [4005-41-8] sigma.com/biofiles [815-92-9] [3573-62-4] Visit C CHO FW 180.16 CHO FW 14 C C 14 14 14 4 FW 180.16 FW 6 E FW 180.16 180.16 FW O 6 [CHOH] 2 O 12 H 12 6 H in ethanol/water (9:1) in ethanol/water (9:1), Ethyl alcohol/water solution (9:1) in ethanol/water (9:1), Ethyl alcohol/water 297569-1UCI G9899-50UCI G9899-100UCI G9899-250UCI 311502-50UCI C 6 -Glucose-6- -Glucose-1- -Glucose-UL- extent of labeling...... 250-360 mCi per mmol mCi per extent of labeling...... 250-360 D C mmol mCi per extent of labeling...... 40-60 at: store D HOCH mmol mCi per extent of labeling...... 45-60 D 14 Packaged in serum bottle Ethanol: water (9:1) solution Ethanol: water serum bottle Packaged in serum bottle
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1 mCi 5 mCi 1 mCi 5 mCi 50 µCi 50 µCi 50 µCi 50 µCi 250 µCi 250 µCi 100 µCi 250 µCi 100 µCi 250 µCi ship: dry ice ship: dry ice ship: dry ice ship: dry ice [4005-41-8] [815-92-9] C CHO FW 180.16 CHO FW 14 C 14 14 4 FW 180.16 FW 6 B B B B O [CHOH] 2 12 H 6 ≥98% as radiochemical purity (HPLC) ≥98% as radiochemical purity (HPLC) ≥98% as radiochemical purity (HPLC) 98% as radiochemical purity (HPLC) ≥98% as radiochemical G5645-50UCI G5770-250UCI G5645-250UCI G5770-50UCI G5020-100UCI G5020-250UCI G5020-1MCI G5020-5MCI G5020-50UCI G4395-50UCI G4395-100UCI G4395-250UCI G4395-1MCI G4395-5MCI C -Glucose-1- -Glucose-UL- extent of labeling...... 2-10 mCi per mmol mCi per extent of labeling...... 2-10 extent of labeling...... 40-60 mCi per mmol mCi per extent of labeling...... 40-60 HOCH D extent of labeling...... 180-360 mCi per mmol mCi per extent of labeling...... 180-360 extent of labeling...... 2-10 mCi per mmol mCi per extent of labeling...... 2-10 D 14 Radioactively-labeled Radioactively-labeled for Glycolysis Metabolites store at: store store at: store Combi-vial store at: store store at: store Combi-vial 10 Pyruvate Transformations sigma.com Figure 2. formation of can beeitherreduced tolactate(2)orethanol(5).Thewell-known reductive conditions,e.g.intheabsenceofoxygen,pyruvate(1) undergo different biotransformationsasshownin is present ornot,pyruvate,aproduct ofglucosemetabolism,can Depending ontheenvironmental conditions,e.g.whetheroxygen Pyruvate Transformations requires NADHasareducing coenzyme. physical activityiscatalyzedbylactatedehydrogenase (LDH)which PyruvateBiotransformations. L -lactate from pyruvateinmusclesduringintense H 3 C H 2 C OH COOH NAD + NADH Figure 2.Under CO H H H 2 3 3 3 C C C H C C 5 O C O 4 1 OH H H COOH hydrogen from NADHtoacetaldehyde. with NADHasreducing coenzyme,alsotransferringthepro-R In thesecondstep,acetaldehydeisthenreduced toethanol(5) using thiamindiphosphateasacofactor. Pyruvate (1)isinthefirststepdecarboxylatedtoacetaldehyde(4) anaerobic conditions. is through theconversionofpyruvatetoethanolbyyeastunder The fundamentalprocess bywhichalcoholicbeveragesare made TPP NADH NAD TPP + CO 2 H 3 C C 3 O SCoA Pyruvate Transformations 11
sigma.com 1 g 1 mg 5 mg 10 mg 25 mg 10 mg 25 mg 10 mg 25 mg 100 mg 100 mg 500 mg 100 mg EC No. 2007909 EC No. EC No. 2423179 EC No. EC No. 2597478 EC No. [32140-51-5] B [18439-24-2] [55672-92-9] FW 809.57 (FA) (FA) 809.57 FW + S FW 785.33 785.33 S FW 3 3 P S FW 767.53 767.53 S FW S · xLi 3 3 16 P P O 16 17 7 O O N B B 7 7 3 2 3 N Li N 36 33 38 R: 36/37/38 S: 26-36/37 store at: store R: 36/37/38 S: 26-36/37 H H H cell culture tested cell culture yeast, ~95% from ~95% (HPLC) C4780-10MG C4780-25MG C4780-100MG C3019-10MG C3019-25MG C3019-100MG C3019-500MG C3019-1G A2181-1MG A2181-5MG A2181-10MG A2181-25MG A2181-100MG 21 21 23 C Approx. 95% Enzymatically assayed using phosphotransacetylase. CoA-SH at: store Coenzyme A trilithium salt CoA Li C at: store Acetyl coenzyme A trilithium salt trilithium A Acetyl coenzyme Li Acetyl-S-CoA C and carrier of acyl groups is an essential cofactor Acetyl-CoA is formed either by the It acetyl transfer reactions. in enzymatic the in mitochondria, by of pyruvate oxidative decarboxylation fatty acids, or by the oxidative degradation oxidation of long-chain in lipid biosynthesis, It is a key precursor of certain amino acids. carbons. It is a positive regulator of all fatty acid and the source of the neurotransmitter It is a precursor of pyruvate carboxylase. acetylcholine. enzymatically Prepared L Coenzyme A hydrate sodium salt CoA Na 1 L 1 mg 5 mg 10 mg 25 mg 100 mL 500 mL 100 mg 0.1 mg/kg 0.1 mg/kg 0.1 mg/kg 0.1 mg/kg 0.5 mg/kg 0.1 mg/kg 0.1 mg/kg 0.5 mg/kg ≤ ≤ ≤ 0.02 mg/kg 0.02 mg/kg ≤ ≤ ≤ ≤ ≤ ≤ ≤ 0.5% ≤ Pb...... Zn...... Li...... Mn...... Mo...... Na...... Ni...... Mg...... Sr...... K...... EC No. 2008368 BRN 505984 BRN 2008368 EC No. [102029-73-2] 0.002% ≤ 0.1 mg/kg 0.1 mg/kg [75-07-0] 0.1 mg/kg 0.5 mg/kg 0.5 mg/kg 0.05 mg/kg 0.02 mg/kg 0.02 mg/kg ≤ ≤ 0.02 mg/kg ≤ ≤ ≤ ≤ ≤ ≤ ≤ COOH)...... 3 S FW 809.57 809.57 S FW 3 P 17 O B E 7 N 38 CHO FW 44.05 CHO FW O...... 100 mg/mL H 3 2 ~95% puriss. p.a., anhydrous, ≥99.5% (GC) puriss. p.a., anhydrous, A2056-5MG A2056-10MG A2056-25MG A2056-100MG A2056-1MG 00070-100ML 00070-500ML 00070-1L 23 Cu...... evapn. residue...... Cd...... Co...... Cr...... Fe...... Ba...... Acetyl-CoA is an essential cofactor and carrier of acyl groups of acyl groups Acetyl-CoA is an essential cofactor and carrier by the It is formed either in enzymatic acetyl transfer reactions. by the oxidative decarboxylation of pyruvate in mitochondria, oxidative degradation oxidation of long-chain fatty acids, or by the in lipid biosynthesis, of certain amino acids. It is a key precursor regulator of all fatty acid carbons. It is a positive and the source of the neurotransmitter of pyruvate carboxylase. It is a precursor acetylcholine. reactions. An essential cofactor in enzymatic acetyl transfer enzymatically Prepared solubility H at: store Acetyl coenzyme A sodium salt Acetyl coenzyme A Acetyl CoA C store at: store (as CH acid free Al...... Acetal dehyde Acetal Ethanal CH Non-labeled Substrates and Substrates Non-labeled for Pyruvate Metabolites Transformations Ca...... Bi...... 12 Pyruvate Transformations sigma.com C K...... Ca...... Bi...... water...... aldehyde (asCH ketone (asCH free alkali(asNH ECNo. 2827338 BRN 5326842 free acid(asCH store at: FAD; FAD-Na Flavin adeninedinucleotide hydrate disodium salt Hygroscopic Al...... KMnO formaldehyde (asHCHO)...... proteases...... none detected phosphatases...... none detected DNases...... none detected RNases...... nonedetected alcohol, withoutadditive) BioChemika Ultra CH Ethyl alcohol Ethanol evapn. residue...... insoluble matter...... passes filtertest Li...... Fe...... Cr...... Co...... Cd...... Ba...... Cu...... substances darkenedbyH methanol (CH 27 F6625-1G F6625-500MG F6625-250MG F6625-100MG F6625-25MG F6625-10MG 51976-500ML ≥95% (HPLC) 3 H CH 31 N 4 2 -reducing substances...... inaccordance OH FW 46.07 9 B Na 2 O 2 ; Ribo flavin 5’-adeno sine di 15 3 3 OH)...... COCH P 3 2 3 COOH)...... ·xH 3 CHO)...... )...... ≤ ≤ ≤ , formolecularbiology, 2 3 ≤ ≤ ≤ ≤ ≤ ≤ 0.02 mg/kg ≤ ≤ 0.02 mg/kg 0.05 mg/kg O FW 829.51 (Anh) )...... 0.5 mg/kg 0.5 mg/kg 0.5 mg/kg 0.1 mg/kg 0.1 mg/kg 0.1 mg/kg 0.1 mg/kg 0.1 mg/kg ≤ [64-17-5] 0.001% 2 SO 4 ...... in accordance ECNo. 2005786 BRN 1718733 Sr...... λ 280nm...... 0.02 260nm...... 0.04 Mg...... Pb...... Ni...... Na...... Mo...... Mn...... Zn...... phos ...... neat phate disodium salt phate disodium [84366-81-4] ≥99.8%, (absolute
≤ ≤ ≤ ≤ 0.02 mg/kg 0.02 mg/kg ≤ ≤ ≤ ≤ 0.1 mg/kg 0.1 mg/kg 0.1 mg/kg ≤ 0.1 mg/kg 0.1 mg/kg ≤ ≤ ≤ 0.0004% ≤ 1 mg/kg 0.001% 0.001% 0.002% 0.001% ≤ 500 mg 250 mg 100 mg ≤ 500 mL 25 mg 10 mg 0.2% 0.1% 1 g CH C sulfate (SO chloride (Cl ign. residue...... <0.1% Phosphorus (P)...... <0.005% matter...... <0.1% Insoluble reduced hydrate disodium salt reduced hydratedisodium β-Nico store at: H solubility ( L store at: BRN 3875902 C chloride Aneurine pyro phos phor Thia store at: α Pyruvic acid Hygroscopic,Light sensitivestore at: Packaged bysolidweight. C Fe...... <0.0005% Cu...... <0.0005% Ca...... <0.0005% Al...... <0.0005% S -(+)-Lactic acid 3 12 21 -Keto pro )-2-Hydroxy L6402-10G L6402-5G L6402-1G C8754-100G C8754-25G C8754-5G C8754-1G 15940-500ML 15940-100ML N8129-5G N8129-1G N8129-500MG N8129-100MG N8129-50MG SigmaUltra, ~98%(titration) ≥97% purum, ~98% (HPLC),(spectrophotometric assay) H 2 3 H H O...... 1 M at 20 °C, clear,at 20°C, O...... 1 M colorless 6 COCOOH FW 88.06 O 19 27 mine pyro 3 ClN N FW 90.08 tin 7 E B E Na 4 pionic acid;2-Oxo O amide adeninedinucleotide, 4 2 ≥98.0% (T) - 2- O )...... <0.05% 7 pro P )...... <0.05% 14 2 S FW 460.77 P pionic acid;Sarco 2 ·xH phos phate [79-33-4] 2 ic acid;Co O FW 709.40 (Anh) pro [127-17-3] pionic acid ECNo. 2011962 BRN 1720251 [154-87-0] carboxy lactic acid E Zn...... <0.0005% Pb...... <0.001% Na...... <0.005% NH Mg...... <0.0005 K...... <0.005% lase; Thia ECNo. 2048243 BRN 506211 4 ECNo. 2052307 + ...... <0.05% mine pyro phos phate 500 mg 100 mg 500 mL 100 mL 50 mg 100 g 10 g 25 g 5 g 1 g 5 g 1 g 5 g 1 g Pyruvate Transformations 13
sigma.com 1 g 1 g inquire inquire inquire inquire 250 mg 250 mg N C O 2 13 N C [70753-79-6] 13 [14770-41-3] O O O 2 2 2 tion 3 O FW 91.07 FW O O FW 93.10 FW O 2 2 O, 98 atom % D atom % O, 98 O, 99 atom % O, 99 solu C 2 2 3 C, 85 wt. % in H C, 85 C C 13 H/H C C 2 13 13 13 2 H / H 13 13 C 2 C C acid (free acid) C acid (free 2 13 CO 13 13 C 13 C acid (free acid) C acid (free OH FW 48.05 OH FW FW 89.05 FW 2 13 3 13 OH FW 47.06 OH FW 2 O CH 4 13 H CH 2 3 3 CH(OH)CO CH(OH) 3 3 99 atom 85 wt. % in H 85 atom % 95% (CP), 99 85 wt. % in H 85 99 atom % 99 atom % 606057 606065 616567 677175 427047-250MG 427047-1G 427039-250MG 427039-1G CC CH CH -Lactic acid- -Lactic acid-3,3,3-d -Lactic acid-1- ]25/D -8.5°, c = 1 in H [α]25/D -8.5°, c = ]25/D -8.5°, c = 1 in H [α]25/D -8.5°, c = 1 in H [α]25/D -8.5°, c = mol wt 93.10 by atom % calculation mol wt 47.06 by atom % calculation mol wt 47.06 Packaged in ampules % calculation mol wt 48.05 by atom L % L CD Pyruvic-1- Pyruvic-1- 13 Ethanol-2- Ethyl alcohol-2- 13 Ethanol- Ethyl alcohol- L CH 13 1 g 1 g 1 g 5 g 1 g inquire 250 mg 500 mg EC No. 2166416 BRN 1743039 2166416 BRN EC No. [14742-23-5] [1632-98-0] 3 [1632-89-9] [19901-15-6] C 2 S FW 829.36 S FW 13 3 C 4 P C C C dehyde 13 -coenzyme A lithium salt -coenzyme A 17 C 2 13 13 13 C O 13 C 7 C 13 13 N 13 acetal 3 Li OH FW 47.06 OH FW 35 2 H CHO FW 46.04 CHO FW CH 21 CHO FW 45.05 CHO FW 13 3 deutero deutero C CDO FW 48.08 CDO FW CHO FW 47.07 CHO FW 13 13 2 3 3 3 3 99 atom % 99 atom % 98 atom % D 99 atom % 98 atom % D 324523-250MG 324523-1G 658650 531227-1G 603805 176567-5G 176567-1G 487767-1G C CH CD mol wt 47.06 by atom % calculation Packaged in ampules mol wt 46.03 by atom % calculation mol wt 45.03 by atom % calculation Hygroscopic Hygroscopic Ethanol-1- Ethyl alcohol-1- 99 atom % Acetyl-1,2- 13 Acetal dehyde- Acetal Acetal dehyde-1- Acetal CH mol wt 48.04 by atom % calculation Tetra Acetal dehyde-d Acetal Hygroscopic, Lachrymator Hygroscopic, Acetal dehyde-2,2,2-d Acetal CD Stable Isotope-labeled Substrates Substrates Isotope-labeled Stable Pyruvate for and Metabolites Transformations 13 CH % calculation mol wt 47.04 by atom 14 Pyruvate Transformations sigma.com CD CH 13 L Sodium L Sodium L Sodium Moisture sensitive [α]25/D -12°,c= 1 inH Packaged asgramofsalt L Sodium [α]25/D -12°,c= 1 inH Packaged asgramofsalt L Sodium mol wt114.03byatom%calculation [α]25/D -12°,c= 1 inH Packaged asgramofsalt mol wt113.05byatom%calculation [α]25/D -12°,c= 1 inH Packaged asgramofsalt CH mol wt113.05byatom%calculation [α]25/D −12°,c= 1 inH Packaged asgramofsalt CH mol wt115.02byatom%calculation mol wt113.05byatom%calculation -Lactic acid-2,3- -Lactic acid-2- -Lactic acid-1- -Lactic-3,3,3-d -Lactic-2-d CH 606006 589209 606022-1G 616702-1G 589217 99 atom % 99 atom % 99 atom % 99 atom % D 98 atom % D 98 atom 3 3 3 3 13 CH(OH) CH(OH)CO CD(OH)CO 3 13 CH(OH)CO CH(OH)CO L L L L L -lactate-3,3,3-d -lactate-2-d -lactate-2,3- -lactate-2- -lactate-1- 1 13 acid sodium salt solution acid sodium CO 13 13 2 2 3 Na FW 115.08 Na FW 113.07 acid sodium salt solution acid sodium C sodium salt solution C sodium C, sodiumsaltsolu 2 2 13 13 13 13 Na FW 113.05 Na FW 113.05 2 C C C C Na FW 114.05 2 sodium salt solution sodium 13 13 1 C solution C solution 13 solution 2 2 2 2 C solu 2 O O O O O 3 solu tion tion tion
N inquire inquire inquire 1 g 1 g CH CH Pyruvic acid-1- Sodium pyruvate-1- 13 L Sodium 13 L Sodium 13 Pyruvic acid-3- Sodium pyruvate-3- Pyruvic acid-2- Sodium pyruvate-2- Moisture sensitive mol wt111.03byatom%calculation S&P tested [α]25/D -12°,c= 1 inH Packaged asgramofsalt mol wt111.03byatom%calculation mol wt111.03byatom%calculation mol wt113.05byatom%calculation -Lactic acid- -Lactic acid-3- CH CH CH 660817 490040-250MG 490733-250MG 490725-500MG 490709-250MG 99 atom % 99 atom 99 atom % 99 atom 99 atom % 99 atom 99 atom % 99 atom % 99 atom 3 3 CO 13 3 3 3 CH(OH)CO COCO COCO 13 13 CH(OH) CO L L -lactate- -lactate-3- 2 2 2 13 Na FW 111.04 Na FW 111.04 Na FW 111.04 13 13 13 C 13 13 3 C sodium salt C sodium C sodium salt C sodium salt C sodium C sodium salt solution C sodium 2 13 13 13 13 13 CO sodium salt solution sodium Na FW 113.05 C C C C C 2 Na FW 115.04 13 C 13 13 13 13 3 C solution solution C C C 2 O [87976-71-4] [124052-04-6] [87976-70-3] [201595-70-2] [201595-71-3] 250 mg inquire 250 mg 500 mg 250 mg Pyruvate Transformations 15
sigma.com 50 µCi 10 µCi 50 µCi 250 µCi H) 3 [4332-37-0] [152585-41-6] B B S FW 809.57 S FW 809.57 S FW C)-coenzyme A C)-coenzyme 3 3 P P 14 17 17 O O 7 7 N N 38 38 H H ≥95% (HPLC) ≥95% (HPLC) A8325-50UCI A8325-250UCI A7925-10UCI A7925-50UCI 23 23 acetate, pH 5.0 Solution in 10 mM sodium Combi-vial 5.0 pH M sodium acetate solution, 0.01 Packaged under Nitrogen Radioactively-labeled Metabolites Radioactively-labeled transformations for Pyruvate (Acetyl-1- C mmol mCi per extent of labeling...... 40-60 at: ship: dry ice store A-(acetyl- Acetyl coenzyme C mmol Ci per extent of labeling...... 5-25 at: ship: dry ice store 1 g 500 mg 500 mg 500 mg [142014-11-7] [89196-78-1] [312623-97-5] 3 2 2 C C 13 13 C,d 3 13 C 13 sodium salt sodium salt sodium salt 2 2 3 C C C C; 50-60 atom % D atom % C; 50-60 C C 13 13 13 13 sodium salt Na FW 113.02 113.02 Na FW 13 13 C,d sigma.com/enzymeexplorer 3 2 Na FW 112.03 112.03 Na FW Na FW 112.03 Na FW 13 C 2 2 Na FW 114.06 Na FW CO 13 2 13 CO Features over 600 detailed procedures for measuring enzyme activity and related metabolites. for measuring enzyme activity and related 600 detailed procedures over Features developed by on analytical procedures of over ten years of in-house work The Library is the result Sigma-Aldrich scientists. Visit the Enzyme Explorer Assay Library Enzyme Explorer Visit 13 CO COCO CO COCO 13 13 3 3 3 13 3 99 atom % 99 atom % 99 atom % 99 atom % 490717-500MG 486191-500MG 493392-500MG 608483-1G CH CH CD mol wt 112.99 by atom % calculation mol wt 112.01 by atom % calculation mol wt 112.01 by atom % calculation mol wt 112.01 by atom mol wt 112.54 by atom % calculation mol wt 112.54 CH Sodium pyruvate- Pyruvic acid- 13 Pyruvic acid-2,3- 13 Sodium pyruvate-2,3- Sodium pyruvate-1,2- Pyruvic acid-1,2- Hygroscopic Hygroscopic Pyruvic acid-3- 13 Sodium pyruvate-3- 16 Citric Acid Cycle sigma.com Figure 3. phosphorylation ofGDPtoGTP. hydrolysis ofthismetabolitetosuccinate(6)iscoupledthe and oxidationis,transformedintosuccinyl-CoA(5).The ketoglutarate (4),which,afteranotherenzymaticdecarboxylation Further enzymaticoxidationanddecarboxylationgives2- a dehydration-hydrationsequencetoyield(2R,3S)-isocitrate(3). to oxaloacetate(1)formingcitrate(2),whichisthenisomerizedby It isstartedbyanenzymaticaldoladditionreaction ofacetylCoA (see Figure 3 also termedthetricarboxylicacidcycle,TCAcycleorKrebs cycle ago markedamilestoneinbiochemistry. Thecitricacidcycleis Acetyl-CoA entersacyclewhosediscoverybyHansKrebs 70years Citric AcidCycle CitricAcidCycle. ). O NAD NaOOC NADH NaOOC NaOOC SCoA H 2 FADH + O H HO 2 1 H SCoA HS O 8 7 COONa COONa COONa FAD NaOOC NaOOC HO hydration catalyzedbyfumaraseis,transformedto dehydrogenase yieldsfumarate(7),which,afterstereospecific Enzymatic desaturationbyFAD-dependent succinate The laststepofNAD-coupledoxidation the cycle. oxaloacetate (1)iscatalyzedbymalatedehydrogenase andcloses 2 COONa COONa COONa 6 NaOOC NaOOC CO CO CoAS SCoA HS 2 2 H HO O OH O COONa COONa COONa 4 COONa 3 5 NADH NAD NADH NAD + + L -malate (8)to L -malate (8). Citric Acid Cycle 17
sigma.com 5 g 1 g 1 g 5 g 1 kg 25 g 25 g 10 g 25 g 100 g 500 g 100 g 100 g 500 g 100 g 10 mg 25 mg 100 mg 500 mg EC No. 2063303 EC No. EC No. 2037430 2037430 EC No. EC No. 2423179 EC No. [328-50-7] [110-17-8] 0.05% [18439-24-2] ≤ dioic acid [1637-73-6] odium salt [997-43-3] pentane S FW 785.33 S FW 3 P COCOOH FW 146.10 COCOOH FW dioic acid potassium salt dioic acid citric acid tris 2 16 ≥99.0% (T) ≥99.5% (T) O FW 258.07 FW 7 CH -Iso 3 s 2 N E E B L glutaric acid potassium salt glutaric acid s 3 K FW 184.19 K FW Na citric acid trisodium salt citric acid D 3 Li 5 7 glutaric acid; 2-Oxo - O O 33 5 5 O...... 0.1 g/mL, clear, colorless O...... 0.1 g/mL, clear, H 2 -Iso H H ≥93% puriss., from yeast, ~95% from puriss., ≥98% (enzymatic) 75890-500G K2000-5G K2000-25G K2000-100G K2000-1KG I1252-1G 75890-25G 75890-100G C3019-10MG C3019-25MG C3019-100MG C3019-500MG C3019-1G 47900-100G 47900-500G I1252-5G I1252-10G I1252-25G I1252-100G 5 6 21 threo BRN 605763 Reagent for the analysis of tryptophan1; Substrate for glutamate Reagent for the analysis of tryptophan1; Substrate dehydrogenase solubility at: store C α-Keto 2-Oxo HOOCCH BRN 1705689 H at: store α-Keto pentane 2-Oxo C Coenzyme A trilithium Coenzyme salt CoA Li C at: store Fumaric acid 116.07 HOOCCH=CHCOOH FW (Lit.) sublimes at 165°C at 1.7 mm pressure DL ign. residue...... ign. residue...... 1 g 5 g 10 g 1 mg 5 mg 1 mg 5 mg 10 mg 25 mg 10 mg 25 mg 100 mg 100 mg EC EC EC No. 2007909 EC No. [585-84-2] [32140-51-5] [102029-73-2] lic acid H FW 174.11 H FW 2 FW 809.57 (FA) (FA) 809.57 FW + isomer upon prolonged storage isomer upon prolonged H)=CHCO 3 2 S · xLi S FW 809.57 S FW 3 3 P P trans 17 17 C(CO O O B B B 2 7 7 pene-1,2,3-tri carboxy pene-1,2,3-tri N N 38 38 CCH O...... 100 mg/mL H H 2 -Aconitic acid 2 -Pro -Pro ~95% ≥98% ~95% (HPLC) A3412-1G A2181-5MG A2181-10MG A2181-25MG A2181-100MG A3412-5G A3412-10G A2181-1MG A2056-1MG A2056-5MG A2056-10MG A2056-25MG A2056-100MG 23 23 Acetyl-CoA is an essential cofactor and carrier of acyl groups cofactor and carrier of acyl groups Acetyl-CoA is an essential It is formed either by the reactions. in enzymatic acetyl transfer of pyruvate in mitochondria, by the oxidative decarboxylation fatty acids, or by the oxidative degradation oxidation of long-chain in lipid biosynthesis, It is a key precursor of certain amino acids. carbons. It is a positive regulator of all fatty acid and the source of the neurotransmitter It is a precursor of pyruvate carboxylase. acetylcholine. enzymatic acetyl transfer reactions. An essential cofactor in enzymatically Prepared solubility May form at: store cis cis 1725829 2095644 BRN No. store at: store Prepared enzymatically Prepared Acetyl-CoA is an essential cofactor and carrier of acyl groups of acyl groups Acetyl-CoA is an essential cofactor and carrier by the It is formed either in enzymatic acetyl transfer reactions. by the oxidative decarboxylation of pyruvate in mitochondria, oxidative degradation oxidation of long-chain fatty acids, or by the in lipid biosynthesis, of certain amino acids. It is a key precursor regulator of all fatty acid carbons. It is a positive and the source of the neurotransmitter of pyruvate carboxylase. It is a precursor acetylcholine. Acetyl coenzyme A trilithium salt Acetyl coenzyme A Acetyl-S-CoA Li C store at: store H Acetyl coenzyme A sodium salt Acetyl coenzyme A Acetyl CoA C Non-labeled Substrates and Substrates Non-labeled Citric Acid for the Metabolites Cycle HO 18 Citric Acid Cycle sigma.com BRN 1705475 Cu...... Insoluble matter...... colorless Al...... EC No. 2448366 BRN 4597521 store at: HOOCCH Keto Oxalo L L- pKa (25 °C)...... (1) 3.46,(2)5.10 L L store at: sulfate (SO H solubility 2-Oxo α-Keto BRN 1723541 Phosphorus (P)...... chloride (Cl Ca...... HO C HOOCCH salt; Sodium2-oxo -Hydroxy -Hydroxy -(−)-Malic acid 4 (−)-Malic acid disodium salt O4126-100G O4126-25G O4126-5G O4126-1G M9138-100G M9138-25G M9138-5G M1000-1KG M1000-500G M1000-100G K2010-100G K2010-25G K2010-5G ~98% 95-100% (enzymatic) SigmaUltra 95-100% (enzymatic) H 2 2 O...... 0.5 M at 20 °C, clear,at 20°C, O...... 0.5 M 4 CCH succinic acid;Oxal O glutaric acid monosodium salt;2-Oxo 5 Na acetic acid glutaric acid sodium salt 2 B E 2 2 CH(OH)CO butane butane 2 COCOOH FW 132.07 CH FW 178.05 4 - 2- )...... 2 )...... COCOONa FW 168.08 dioic acid dioic acid;( glutarate monobasic 2 H FW 134.09 acetic acid;Oxo ≤ ≤ ≤ 0.0005% ≤ 0.0005% 0.0005% ≤ ≤ 0.001% S ≤ [138-09-0] 0.05% 0.05% )-(−)-2-Hydroxy 0.1% [328-42-7] butane K...... Zn...... Mg...... Pb...... Fe...... NH [97-67-6] [22202-68-2] pentane 4 succinic acid + ...... dioic acid;2-Oxo ECNo. 2063298 ECNo. 2026015
dioic acid monosodium
succinic acid ≤ ≤ ≤ ≤ 0.0005% ≤ 0.0005% 0.0005% ≤ 0.001% 0.005% 0.05% 100 g 100 g 500 g 100 g 100 g 25 g 25 g 25 g 1 kg 5 g 1 g 5 g 5 g BRN 4301302 RTECS #LT1830000RTECS Hygroscopic water...... ~0.5% NaOOCCH=CHCOONa FW 160.04 Disodium fumarate;Fumaricacid disodium salt Sodium fumaratedibasic [α] (1R,2S)-1-Hydroxy-1,2,3-propane (+)-Potas store at: C Succinyl coenzyme A sodium salt Substrate forthecharacterizationofisocitratedehydrogenase1 C D 6 s 25 47970-500G-F 47970-100G-F 58790-1G 58790-250MG S1129-25MG S1129-5MG -(+)- puriss., anhydrous, purum, Minimum 85% H 20/D +20.5±1°,c= 2 inH H 7 KO 40 threo N 7 7 FW 230.21 B O 19 sium D ≥ P -Iso 3 98.0% (NT) S FW 867.61 citric acid monopotassium salt s -threo [20226-99-7] ≥99.0% (NT) -isocitrate mono [108347-97-3] tri carboxy 2 O BRN 3767339 [17013-01-3] lic acid monopotassium salt; basic ECNo. 2410877 250 mg 25 mg 500 g 100 g 5 mg 1 g Citric Acid Cycle 19
sigma.com 1 g 5 g inquire inquire inquire inquire 100 mg 100 mg [14493-42-6] 6 4 4 3 2 H FW 120.04 H FW 124.07 D FW 6 2 2 H FW 135.08 H FW 4 C 2 H FW 137.11 H FW 13 D FW 152.14 D FW H FW 118.06 H FW C ,d 2 CO CO 2 2 4 4 13 dioic acid-d 13 13 C C C D atom % C; 98 C C H FW 122.11 H FW 2 13 13 13 13 13 13 CH CD CHCO 13 13 COCO CO 2 2 13 CH(OH)CO 13 CD CD(OH)CO CD CH= CD= 2 2 2 2 CH= 13 13 pentanoic acid-d dioic acid-2,2,3,3-d C C 13 13 13 CCD CCD CCH CCD C 2 2 2 2 2 2 2 Keto -Malic acid-2- -Malic acid-2,3,3-d 98 atom % D 98 atom % D 99 atom % 99 atom % 99 atom % 99 atom % 98 atom % D 293075-1G 293075-5G 615390 641049 603899 606073-100MG 606014-100MG 608475 mol wt 135.08 by atom % calculation mol wt 118.04 by atom % calculation mol wt 118.04 % calculation mol wt 120.01 by atom mol wt 123.99 by atom % calculation DO mol wt 152.02 by atom % calculation DL HO mol wt 137.05 by atom % calculation DL HO Succinic acid-2,2,3,3-d Butane HO Hygroscopic Fumaric acid-2,3- HO Fumaric acid- HO Fumaric acid- DO pentane 2-Keto α- mol wt 122.08 by atom % calculation 5 g 5 g 1 g inquire 100 mg 100 mg 100 mg [121633-50-9] [302912-06-7] [147664-83-3] [194160-45-7] [24461-32-3] H FW 194.11 194.11 H FW 2 FW 198.08 FW CO 2 2 H) 2 CH FW 194.11 FW 13 2 4 FW 196.15 FW CO 2 2 H) H) 13 2 2 2 2 S FW 829.36 S FW 2 H) 3 2 C C P C C C 4 CO 13 13 CH -coenzyme A lithium salt -coenzyme A D FW 120.10 D FW H FW 118.08 H FW 17 2 13 13 13 2 2 6 CO 13 13 C O 2 2 C C 7 13 13 N 13 H)( 3 2 C(OH)(CO Li 2 H)(CH H)(CD 35 CO 2 2 H CH 13 21 13 C( C CCD=CDCO CCD=CDCO C 2 2 2 13 2 98 atom % D 98 atom % D 99 atom % 98 atom % D, 98% ( CP) 99 atom % 99 atom % 485713-5G 486671-5G 606081-100MG 492078-100MG 488607-100MG 485438-1G 658650 C mol wt 120.06 by atom % calculation mol wt 118.06 by atom % calculation mol wt 196.07 by atom % calculation mol wt 196.07 by atom 97% (CP) mol wt 198.02 by atom % calculation mol wt 194.09 by atom % calculation mol wt 194.09 by atom % calculation DO Fumaric acid-d HO Fumaric acid-2,3-d Citric acid- HO Citric acid-2,4- HO Citric acid-1,5- HOC(CO Citric acid-2,2,4,4-d HOC(CO 99 atom % Acetyl-1,2- 13 Stable Isotope-labeled Substrates Substrates Isotope-labeled Stable Acid the Citric for and Metabolites Cycle 20 Citric Acid Cycle sigma.com mol wt124.07byatom%calculation HO Butane Succinic acid-2,3- HO Butane Succinic acid-1,4- HO Butane Succinic acid-1,2- DO Butane Succinic acid-d mol wt120.16byatom%calculation mol wt120.16byatom%calculation mol wt120.16byatom%calculation 488364-100MG 485349-500MG 491977-100MG 488356-5G 98 atom % D 98 atom 99 atom % 99 atom % 99 atom % 99 atom 2 2 2 2 13 C CCH C(CD 13 CCH dioic acid-2,3- dioic acid-1,4- dioic acid-1,2- dioic acid-d CH 2 2 13 ) 2 2 2 CH CH 13 CO New! ■ ■ ■ Currently inDevelopment 73 CarbohydratesandMetabolicIntermediates 70 AminoAcidsandMetabolicIntermediates Libraries Available —ChooseFrom: Metabolomics Web Resource. Choose yourowncomponents,andbuildacustomlibraryonlineusingtheSigma-Aldrich Individually packagedstandards inautosamplervialsformetabolomicanalysis. New 10mgpackagesizesofMetaboliteStandards representative formore details. container specificationstofityourspecific requirements. ContactyourSAFCsales Sigma-Aldrich offers custompackaging ofmetabolitestandards withvialcontentand Custom PackagingCapabilities the SigmaGeneralCatalogoronline(sigmaaldrich.com/metabolites). Hundreds ofothermetabolitesare availableinstandard packagingandcanbefoundin CH Visit Vitamin/Cofactor Library Vitamin/Cofactor NucleotideLibrary LipidLibrary 2 2 2 13 13 D FW 124.13 2 13 13 13 CO CO CO sigma.com/metpath 6 C C C 6 2 2 2 13 13 13 H FW 120.07 H FW 120.07 H FW 120.07 13 13 13 C C C C C C MetaboliteLibraries 2 2 2 2 2 2 [21668-90-6] [61128-08-3] [79864-95-2] [94641-55-1] 100 mg 500 mg 100 mg 5 g serum bottle Ethanol: water(1:1)solution HO Succinic acid-2,3- extent oflabeling...... 1-10 mCi per mmol HOOC Fumaric acid-2,3- store at: extent oflabeling...... 40-60 mCi per mmol HOO Citric acid-1,5- fot theCitricAcidCycle Radioactively-labeled Metabolites extent oflabeling...... 1-15 mCi per mmol HO Succinic acid-carboxy- store at: extent oflabeling...... 20-40 Ci per mmol Packaged inscrew-cap bottle sealed ampule Packaged inscrew-cap bottle 304735 C2916-250UCI C2916-50UCI 305006 S2174-1MCI S2174-250UCI ≥95% (RadiochemicalPurity) 2 2 CC 14 14 CCH 14 CCH 3 H CH= E E 2 C 2 2 CH 3 C[OH][COOH]CH 14 H CHCOOH FW 116.07 2 2 CO 14 CO 14 2 C H FW 118.09 2 3 14 H H C [13613-74-6] 14 C 2 14 COOH FW 192.12 [3073-84-5] [54744-93-3] [58308-53-5] 304735 1 250 µCi 250 µCi inquire 50 µCi 1 mCi Monosaccharide Biosynthesis 21
sigma.com ONa ONa ONa O 4 O 5 P O OH O OH NaO OH O O O OH P 12 HO HO HO NaO NaO O 2 ONa H O P O NaO ONa 8 O O 3 O PONa O ONa ONa P C ONa 2 O O OH ONa HO H P O OH 2 -Glyceraldehyde-3-phosphate (7) tautomerizes to (7) tautomerizes -Glyceraldehyde-3-phosphate OH O NaO dihydroxyacetone phosphate (8) and the condensation of these (8) and the condensation phosphate dihydroxyacetone (9) is units to fructose-1,6-bisphosphate two three-carbon aldolase. a class I aldolase, fructose-1,6-bis-phosphate catalyzed by catalyzed by fructose-1,6-bisphosphatase reaction A hydrolysis at C1 and yields fructose-6- the phosphate group removes further tautomerizes to glucose-6- phosphate (10), which phosphate (11). (12) is catalyzed by step to glucose The final hydrolysis phosphatase. also of importance monosaccharides are The pathways of other metabolites states. Sigma offers to both healthy and pathological fructose and interconversions, pentose and glucuronate from galactose metabolism, ascorbate and mannose metabolism, metabolism, amino- and sucrose and aldarate metabolism, starch inositol and other monosaccharide nucleotide sugar metabolism, metabolic pathways. D O CO OH 9 HO GDP O O 11 O HO OH ONa OH P O GTP 6 O O O ONa H NaO -3- ONa P OH P D O O O OH NaO OH O 2 NaO NaO HO O 7 O + OH O NADH P NAD O HOOC NaO ONa NaO + P 10 ADP H O - 3 Figure 4). Figure NaO ATP HCO ONa O -3-phosphoglycerate with ATP ATP -3-phosphoglycerate with 1 O D C 3 H -1,3-bisphospho-glycerate (6), which after reduction (6), which after reduction -1,3-bisphospho-glycerate Monosaccharide Biosynthesis. D -glyceraldehyde-3-phosphate (7). D -2-phosphoglycerate (4), which is converted through a which is converted through -2-phosphoglycerate (4), produces produces phospho-glycerate (5). of Another phosphorylation sequence of phosphorylation at the primary hydroxyl group and and group at the primary hydroxyl sequence of phosphorylation gives group the secondary hydroxyl a dephosphorylation at leads to Figure 4. Figure D Each of the monosaccharides has its own interesting metabolism. its own interesting monosaccharides has Each of the the is made, is not by which a monosaccharide The pathway pathway (see of its degradation reverse Monosaccharide Biosynthesis Monosaccharide Glucose biosynthesis starts with the carboxylation of pyruvate (1) carboxylation of pyruvate starts with the Glucose biosynthesis by pyruvate carboxylase requiring to oxaloacetate (2) catalyzed and biotin as coenzymes. ATP phosphorylation of oxaloacetate (2) is The decarboxylation and pyruvate carboxykinase and utilizes catalyzed by phosphoenol energy-rich phosphoenolpyruvate (3). and GTP to yield both ATP of water to the double bond of Enolase-catalyzed addition and gives occurs stereospecifically phosphoenolpyruvate (3) 22 Monosaccharide Biosynthesis sigma.com C phos phosphate (PO C pH...... 3.5-4.5, 0.5 g/10 mLH2Oat25 °C store at: D as asubstrate. Unlike thedimethylketal,doesnotrequire hydrolysis priortouse Enzymatically prepared. DHAP; 1,3-Dihydroxy-2-propan one 1-phos Dihydroxy store at: H [α]20/D +34±1°,c= 10 inH dehydrogenase, EC1.1.1.491 Substrate forthedeterminationofglucose-6-phosphate D D store at: H solubility BRN 4611329 C Tris Phos Monosaccharide Biosynthesis Non-labeled Metabolitesfor solubility BRN 5787568 -glyceraldehyde 3-phosphate...... ~0.2 mol % (+)-Gluco -Glucose 6-phos 3 3 6 D7137-250MG D7137-100MG D7137-25MG D7137-10MG D7137-5MG 49282-5G 49282-1G 49282-250MG 79435-500MG ≥95% (enzymatic) BioChemika BioChemika H H H 2 2 odium phos O...... 50 mg/mL, clear, colorlesstoveryfaintlyyellow O...... 0.1 g/mL, clear toslightlyturbid,colorless 12 2 5 phate; 1-Hydroxy-3-(phos Li Na NaO pho(enol)pyruvic acid heptahydrate trisodium salt acid heptahydratetrisodium pho(enol)pyruvic 2 O 3 O B E B 6 P FW 181.92 9 6 pyran P FW 282.12 P ·7H acetone phos pho 4 ose 6-phos - , crystallized,anhydrous, , 2 )...... ~5 mol % O FW 360.09 ≥97.0% (enzymatic) enolpyruvate heptahydrate phate sodium salt phate sodium [102783-56-2] phate sodium salt;G-6-PNa;Robisonester [54010-71-8] phate dilithium salt phate dilithium phono oxy)-2-propan 2 O [5541-93-5] phate dilithium salt; Gly salt; phate dilithium ECNo. 2589210 BRN 1708891 ≥98.0% (enzymatic) ECNo. 2269068 one dilithium salt one dilithium cero ne 250 mg 100 mg 250 mg 500 mg 25 mg 10 mg 5 mg 5 g 1 g BRN 1705475 C D store at: Keto Oxalo ship: dryicestore at: Ba...... C DL store at: (−)-Disodium D- store at: C HOOCCH (−)3-Phos pho gly 3 3 3 O4126-100G O4126-25G O4126-5G O4126-1G G5251-1G G5251-500MG G5251-250MG G5251-100MG G5251-25MG P8877-5G P8877-1G P8877-10MG P0769-1G P0769-10MG (−)-3-Phos pho gly ~95% ~98% ~95% 45-55 mg/mL in H in 45-55 mg/mL H H H -Gly 7 5 4 succinic acid;Oxal O Na O 6 7 P FW 170.06 PNa acetic acid cer 2 O B B B 2 7 COCOOH FW 132.07 P FW 230.02 alde 3 FW 252.00 D -3-phos pho hyde 3-phos ceric acid trisodium salt acetic acid;Oxo B ceric acid disodium salt ≤ 2 [591-59-3] O 100 µg/mL gly cer ate; [80731-10-8] [6134-04-9] phate solution D [328-42-7] -Gly cer butane BRN 3767836 ate 3-phos dioic acid;2-Oxo ECNo. 2063298 phate disodium salt phate disodium succinic acid 500 mg 250 mg 100 mg 25 mg 10 mg 10 mg 100 g 25 g 5 g 1 g 1 g 5 g 1 g 1 g Monosaccharide Biosynthesis 23
sigma.com 1 g 1 g 100 mg 250 mg 500 mg 250 mg 100 mg 500 mg 250 mg 100 mg 500 mg OH) OH) OH) OH) OH) 4 4 4 4 4 [30737-83-8] BRN 5810734 BRN [106032-61-5] [89196-78-1] O (trace NH O (trace NH O (trace NH O (trace NH O (trace NH 2 2 2 2 2 2 C [138079-87-5] [287100-67-8] 13 [106032-62-6] 2 2 sodium salt 2 C C C C C C C 13 13 C 1 1 2 2 13 13 13 13 13 CDO FW 181.16 CDO FW CDOHCHO FW 181.16 181.16 FW CDOHCHO 13 C C 4 3 Na FW 112.03 Na FW 2 13 13 C 1 1 FW 182.14 FW 182.14 FW 6 6 FW 181.15 181.15 FW 13 6 O O O 12 12 COCO 12 [CHOH] [CHOH] H H 2 2 13 4 4 H 3 5 C C 2 2 99 atom % 98 atom % 98 atom % D 99 atom % 99 atom % 98 atom % D 453196-100MG 453196-250MG 486191-500MG 310816-250MG 310816-1G 453188-100MG 453188-500MG 310824-250MG 310824-1G 310808-100MG 310808-500MG CH C C CC -Glucose-1,2- -Glucose-1,6- -Glucose-2-d -Glucose-6- -Glucose-1-d ]25/D +52.0°, c = 2 in H c = [α]25/D +52.0°, mol wt 112.01 by atom % calculation mol wt 182.12 by atom % calculation mol wt 182.12 by atom % calculation mol wt 181.14 by atom % calculation Sodium pyruvate-2,3- Pyruvic acid-2,3- 13 HOCH Hygroscopic Dextrose-1,2- D Dextrose-1,6- Hygroscopic D Dextrose-2-d HOCH Hygroscopic D Dextrose-6- 13 2 in H [α]25/D +52.0°, c = D Dextrose-1-d D 13 13 mol wt 181.16 by atom % calculation % calculation mol wt 181.16 by atom 2 in H [α]25/D +52.0°, c = ]25/D +52.0°, c = 2 in H [α]25/D +52.0°, c = 2 in H [α]25/D +52.0°, c = 1 g 1 g 1 g 2 g 3 g 1 g 10 g 10 g 250 mg 250 mg 100 mg 250 mg 100 mg 500 mg OH 4 OH) OH) OH) 4 4 4 BRN 2263682 BRN O (trace NH O (trace NH O (trace NH 2 2 2 C 13 [105931-74-6] [40762-22-9] [18991-62-3] [110187-42-3] 2 C C C C C 13 13 13 6 -Glucose-ul- 13 13 D 2 C ; C C 13 6 FW 181.15 FW FW 181.15 FW 13 13 C 6 6 FW 182.17 182.17 FW FW 186.11 FW 6 13 6 O O O O 12 12 10 H H 12 5 5 H H 2 6 D 98 atom % D 99 atom % 99 atom % 99 atom % 310794-250MG 310794-1G 297046-250MG 297046-1G 389374-100MG 389374-250MG 389374-1G 389374-2G 389374-3G 389374-10G 297046-10G 282650-100MG 282650-500MG 282650-1G CC CC C 6 -Glucose-2- -Glucose-1- -Glucose- -Glucose-6,6-d ]25/D +52.0°, c = 2 in H [α]25/D +52.0°, c = % calculation mol wt 182.15 by atom ]25/D +52.0, c = 2 in water + trace NH 2 in water + trace [α]25/D +52.0, c = mol wt 181.14 by atom % calculation mol wt 181.14 by atom % calculation mol wt 186.05 by atom % calculation Dextrose-2- 13 Dextrose-1- 13 2 in H [α]25/D +52.0°, c = Hygroscopic Hygroscopic D Dextrose- 13 Hygroscopic Hygroscopic C D D D Dextrose-6,6-d Stable Isotope-labeled Isotope-labeled Stable for and Metabolites Substrates Biosynthesis Monosaccharide ]25/D +52.0°, c = 2 in H [α]25/D +52.0°, c = 24 Monosaccharide Biosynthesis sigma.com CH CH 13 Hygroscopic 13 Phos Hygroscopic Dextrose- D CH Pyruvic acid-1,2- Sodium pyruvate-1,2- 13 Pyruvic acid-3- Sodium pyruvate-3- Pyruvic acid-2- Sodium pyruvate-2- 13 Pyruvic acid- Sodium pyruvate- Moisture sensitive Pyruvic acid-1- Sodium pyruvate-1- mol wt207.12byatom%calculation mol wt192.88byatom%calculation mol wt112.01byatom%calculation mol wt111.03byatom%calculation mol wt111.03byatom%calculation mol wt112.99byatom%calculation mol wt111.03byatom%calculation [α]25/D +52.0°,c= 2 inH -Glucose- CC C CH CH 571237-50MG 552151-5G 552151-1G 552151-500MG 493392-500MG 490733-250MG 490725-500MG 490717-500MG 490709-250MG 99 atom % 99 atom 99 atom % 99 atom 99 atom % 99 atom 99 atom % 99 atom 99 atom % 99 atom % 99 atom % 99 atom 3 3 3 6 13 13 CO H 3 3 2 13 H 5 CO COCO COCO pho(enol)pyruvic acid-3- D 13 4 CO KO 7 13 CO O 13 13 6 CO C 6 FW 193.15 P FW 207.13 2 2 2 13 CO 6 13 Na FW 111.04 Na FW 111.04 Na FW 111.04 ,C-d 2 C 13 13 13 C Na FW 112.03 2 3 C sodium salt C sodium salt C sodium salt C sodium 6 13 Na FW 113.02 sodium salt sodium 13 13 13 13 13 13 13 ,C-d 7 C C C; 97-99 atom % D C C C C C ; 2 D sodium salt sodium -Glucose- 7 13 C 13 13 13 3 C C C [201417-01-8] 13 C 2 2 13 O (traceNH C [124052-04-6] [87976-70-3] [87976-71-4] 6 [312623-97-5] ,1,2,3,4,5,6,6-d 13 [142014-11-7] C potassium salt C potassium N 4 OH) 7 500 mg 500 mg 250 mg 500 mg 500 mg 250 mg 50 mg 5 g 1 g mol wt192.11byatom%calculation mol wt181.15byatom%calculation 13 13 [α]25/D +52.0°,c= 2 inH Dextrose-2,5- D [α]25/D +52.0°,c= 2 inH Dextrose-4,5- D [α]25/D +52.0°,c= 2 inH 13 Dextrose-3- D 13 D Hygroscopic [α]25/D +52.0°,c= 2 inH C Dextrose-d D [α]25/D +52.0°,c= 2 inH C Dextrose-3-d D Hygroscopic 13 Pyruvic acid-3- Sodium pyruvate-3- mol wt182.12byatom%calculation mol wt182.12byatom%calculation mol wt181.14byatom%calculation [α]25/D +52.0°,c= 2 inwater+traceNH mol wt112.54byatom%calculation -Glucose-2,5- -Glucose-4,5- -Glucose-3- -Glucose-4- -Glucose-d -Glucose-3-d 6 6 C C CC CC CD 605468 605409 668648 616338-250MG 615498 608483-1G 605506 99 atom % 99 atom % 99 atom % 99 atom 97-99 atom % D 97-99 atom 99 atom % 99 atom % D 98 atom % 99 atom D DH 2 2 12 C C 5 5 3 11 4 4 H H O COCO H H 12 12 O 6 12 12 FW 192.23 6 O O FW 181.16 O O 6 6 12 13 6 6 FW 181.15 FW 181.15 2 FW 182.14 FW 182.14 1 Na FW 114.06 C 13 13 13 12 C C 13 13 C,d 13 13 13 13 13 2 2 1 C C 13 13 C C C C C; 50-60 atom % D C C 3 sodium salt sodium 2 2 13 C,d 2 2 2 2 2 3 O (traceNH O (traceNH O (traceNH O (traceNH O (traceNH N 4 4 4 4 4 OH) OH) OH) OH) OH) 4 OH 250 mg inquire inquire inquire inquire inquire 1 g Pentose Phosphate Pathway 25
sigma.com 2 OH Na 3 OH PO H HO O OH O 2 O 2 H OH OH OH 2 -glyceraldehyde-3-phosphate (8) -glyceraldehyde-3-phosphate 7 OH OH D CH CH Na 3 OH 11 H O PO 9 ONa HO -glyceraldehyde-3-phosphate (8). -glyceraldehyde-3-phosphate P D O 8 O 2 OH ONa O P O ONa CH O NaO H OP ONa H NaO OH 2 10 2 HO Na O 3 Na 3 OH PO PO O O 2 OH and fructose-6-phosphate is channelled through fructose-1,6- is channelled through and fructose-6-phosphate bisphosphate (10). An additional link between An additional link between Growing and dividing cells require ribose-5-phosphate, but excess but excess ribose-5-phosphate, cells require and dividing Growing (6), a with xylulose-5-phosphate (5) reacts ribose-5-phosphate leads to glyceraldehyde- transketolase, which catalyzed by reaction (7) as products. (8) and sedoheptulose-7-phosphate 3-phosphate of sedo- reaction In the next step, the transaldolase-catalyzed (7) with glyceraldehydes-3-phosphate (8) heptulose-7-phosphate and fructose-6-phosphate (11). (9) yields erythrose-4-phosphate pathway involves again xylulose-5- One closing step of this (9), but in this step the phosphate (6) and erythrose-4-phosphate two-carbon unit transfer gives fructose-6- transketolase-catalyzed phosphate (11) and OH O ONa 2 2 H OH P CH O CH CH H H 8 H NaO 6 2-Deoxy- D-ribos e- 5-phos phate HO O OH O 2 2 OH NADP NADP H NADPH NADPH OH CH COONa O OH O OH O O OH OH OH OH OH OH O HO O HO ONa OH ONa P OH O 4 2 P 5 1 O 2 OH OH O ONa CO P 3 O NaO O ONa NaO P O O NaO ONa D-Ribose D-Ribose- PRPP 1-phosphate P NaO O NaO Pentose Phosphate Pathway. Figure 5). Figure Figure 5. Figure While glucose metabolism by glycolysis occurs where energy is energy occurs where metabolism by glycolysis While glucose cells, a second pathway in brain and muscle e.g. needed quickly, phosphate pathway, metabolism, called pentose for glucose fatty acids and steroids tissues that synthesize operates in (see is phosphorylated at the 6-position to As in glycolysis, glucose (1). give glucose-6-phosphate at the anomeric center is catalyzed NADP-dependent oxidation and yields dehydrogenase by glucose-6-phosphate yields the (2), which upon hydrolysis 6-phosphogluconolactone 6-phosphogluconate (3). group oxidation at the C3-hydroxy Another NADP-dependent to ribulose-5-phosphate (4). transforms 6-phosphogluconate xylulose-5-phosphate (6) formation leads to either Tautomerization epimerase or to ribose-5- catalyzed by ribulose-5-phosphate which is catalyzed by ribulose-5- phosphate (5) formation, phosphate isomerase. Pentose Phosphate Pathway Phosphate Pentose 26 Pentose Phosphate Pathway sigma.com suitable forsubstratetransaldolase C C pH...... 3.5-4.5, 0.5 g/10 mLH store at: D 6-Phos pho ship:dry icestore at: Ba...... C DL store at: H [α]20/D +34±1°,c= 10 inH dehydrogenase, EC1.1.1.491 Substrate forthedeterminationofglucose-6-phosphate D D store at: 4-Phos pho- D Pentose PhosphatePathway Non-labeled Metabolitesfor solubility C salt acid tris(cyclohexylamine) -Gluco (+)-Gluco -Erythrose 4-phos -Glucose 6-phos 4 6 3 6 P7752-1G P7752-500MG P7752-100MG G5251-1G G5251-500MG G5251-250MG G5251-100MG G5251-25MG 49282-5G 49282-1G 49282-250MG E0377-250MG E0377-100MG E0377-25MG E0377-10MG E0377-5MG 60-75% Grade V BioChemika 45-55 mg/mL in H in 45-55 mg/mL 2 H H H H -Gly O...... 50 mg/mL, clear, colorlesstoveryfaintlyyellow 12 8 13 7 O NaO O NaO 6 10 P FW 170.06 cer nate 6-phos B E B P ·3C 7 9 P FW 222.07 pyran P FW 282.12 alde D -erythrose sodium salt -erythrose sodium gluconic acid tri(cyclohexylammonium) salt 6 H ose 6-phos hyde 3-phos , crystallized,anhydrous, 13 N FW 573.66 phate tris(cyclohexylamine) salt;6-Phos phate sodium salt phate sodium B phate sodium salt phate sodium ≤ 2 [591-59-3] O 100 µg/mL [54010-71-8] phate sodium salt;G-6-PNa;Robisonester [103302-15-4] phate solution 2 O [108347-81-5] ECNo. 2589210 BRN 5787568 2 ≥98.0% (enzymatic) O at25 °C pho gluconic 500 mg 100 mg 500 mg 250 mg 100 mg 250 mg 250 mg 100 mg 25 mg 25 mg 10 mg 5 mg 1 g 1 g 5 g 1 g solvent (ethanol,methanol)...... D store at: H C D store at: D 6-Phos pho Xu 5-PC D store at: Ru-5-P C D S: 22-24/25store at: ethanol...... H solubility C D EC No.242-140-7store at: D solubility Isolation oftransketolase For thesynthesisof5-phospho-D-ribosyl C C -Gluco -Ribo furan -Ribo -Xylulose 5-phos -Ribulose 5-phos -Ribulose 5-phos -Ribo 5 6 5 5 83875-1G 83875-250MG P7877-5G P7877-1G P7877-500MG P7877-100MG X0754-25MG X0754-5MG R9875-25MG R9875-5MG 83899-100MG 83899-25MG 83899-5MG R7750-5G R7750-1G R7750-250MG R7750-10MG ~90% Grade IV, BioChemika BioChemika ≥98% BioChemika H H H H 2 2 O...... 50 mg/mL, clear,O...... 50 mg/mL, colorless O...... 50 mg/mL, clear, lightyellowmethanol.... 9 10 9 9 Na Na Na Na 2 2 2 nate 6-phos se 5-phos se 5-phos O 3 O O B B B O 8 8 8 P ·2H 10 P FW 274.07 P ·xH 5 5 ose 5-phos H H P FW 342.08 gluconic acid trisodium salt 11 10 ≥97% (enzymatic) O NaO 2 8 , ~30%(enzymatic) , , 2 O FW 274.07 (Anh) ECNo. 2421407 BRN 4774244 P FW 230.11 O FW 310.10 ≥96% (TLC) ≥99.0% (TLC) 8 phate dihydrate disodium salt phate dihydratedisodium phate hydrate disodium salt phate hydratedisodium phate trisodium salt phate trisodium P FW 252.09 B phate sodium salt phate sodium salt phate disodium phate sodium salt phate sodium phate disodium salt phate disodium [53411-70-4] B ≤ 2% water...... <10% [108321-99-9] [207671-46-3] [105931-44-0] N ECNo. 2585436 BRN 3814212 α-1-pyrophosphate; ≤ 5% 250 mg 500 mg 100 mg 100 mg 250 mg 25 mg 25 mg 25 mg 10 mg 5 mg 5 mg 5 mg ≤ 1 g 5 g 1 g 5 g 1 g 1%
Calvin Cycle 27
sigma.com - D -sedoheptulose- D -sedoheptulose- D H 2 O Na 3 OH PO OH 8 -erythrose-4-phosphate (8). -erythrose-4-phosphate both of -ribose-5-phosphate (11), O ONa D D O OH O 2 2 H OH OP ONa O ONa CH CH OH P -glyceraldehyde-3-phosphate yields yields -glyceraldehyde-3-phosphate 6 D O H -glyceraldehyde-3-phosphate gives again -glyceraldehyde-3-phosphate HO D O 7 HO NaO OH ONa ONa O P ONa O P 2 O O 2 2 CH ONa Na 2 Hexose Synthesis Hexose Na 3 ONa NaO 3 P Na O 3 ONa PO O PO O OH O PO O O O O OH -xylulose-5-phosphate (7) and -xylulose-5-phosphate (10). -sedoheptulose-7-phosphate (7) and -xylulose-5-phosphate OH 2 1 2 H ONa OH OH OH 1,7-bisphosphate (9), which after enzymatic hydrolysis, yields after enzymatic hydrolysis, 1,7-bisphosphate (9), which The next transketolase-catalyzed reaction of of reaction The next transketolase-catalyzed A transketolase-catalyzed two-carbon unit transfer from unit transfer from two-carbon A transketolase-catalyzed D D D Aldol condensation of erythrose-4-phosphate (8) with (8) of erythrose-4-phosphate Aldol condensation produces (5) dihydroxyacetone-phosphate 7-phosphate (10) and (12). enzymatically isomerized to ribulose-5-phosphate which are to ribulose-1,5-bisphosphate (1) by This is then converted back the Calvin cycle. completing phosphorylation with ATP, fructose-6-phosphate to fructose-6-phosphate OH O 9 O 2 CH P OH O CH O O 2 CH O 3 O H ONa NaO O P P H P H HO O 4 O NaO NaO NaO NaO 5 NaO HO O OH 2 2 CH Na 3 OH O PO OH O O O OH 2 OH 2 H OH OH OH OH OH CH CH Figure 6). Figure O -ribulose-1,5-bisphosphate (1) -ribulose-1,5-bisphosphate 10 O D H ONa ONa 11 P P 12 HO O O -glyceraldehyde-3-phosphate (4) -glyceraldehyde-3-phosphate D NaO NaO -fructose-1,6-bisphosphate (6) and -fructose-1,6-bisphosphate D -1,3-bisphosphoglycerate (3) upon -1,3-bisphosphoglycerate D -fructose-6-phosphate. -fructose-6-phosphate. D Calvin Cycle. -3-phosphoglycerate (2). -3-phosphoglycerate (2). upon reduction with NADPH. upon reduction isomerization to dihydroxyacetonephosphate The next steps are to (5), aldol condensation further hydrolysis to further hydrolysis This compound yields Figure 6. Figure The fixation of carbon dioxide with The fixation of carbon D The Calvin cycle is a more complex process used by algae, plants used complex process is a more The Calvin cycle water carbon dioxide and bacteria to convert and photosynthetic sunlight. with the aid of and molecular oxygen into carbohydrate reducing molecular oxygen and split water into The light reactions reduce while the dark reactions power in the form of NADPH, (see carbon dioxide to carbohydrates Calvin Cycle Calvin is catalyzed by ribulose-1,5-bisphosphate carboxylase and yields is catalyzed by ribulose-1,5-bisphosphate phosphorylation with ATP and phosphorylation with ATP 28 Calvin Cycle sigma.com suitable forsubstratetransaldolase C C store at: C D store at: (−)-Disodium D- ship: dryicestore at: Ba...... C DL store at: 4-Phos pho- D Calvin Cycle Non-labeled Metabolitesfor -Erythrose 4-phos (−)3-Phos pho gly 4 3 3 3 P0769-1G P0769-10MG P8877-5G P8877-1G P8877-10MG G5251-1G G5251-500MG G5251-250MG G5251-100MG G5251-25MG E0377-250MG E0377-100MG E0377-25MG E0377-10MG E0377-5MG (−)-3-Phos pho gly 60-75% ~95% ~95% 45-55 mg/mL in H in 45-55 mg/mL H H H H -Gly 5 7 8 4 O Na O NaO 7 6 PNa P FW 170.06 cer 2 O B B B 7 7 P FW 222.07 P FW 230.02 alde 3 D FW 252.00 -erythrose sodium salt -erythrose sodium D -3-phos pho hyde 3-phos ceric acid trisodium salt B ceric acid disodium salt phate sodium salt phate sodium ≤ 2 [591-59-3] O 100 µg/mL gly cer ate; [103302-15-4] [80731-10-8] [6134-04-9] phate solution D -Gly cer BRN 3767836 ate 3-phos phate disodium salt phate disodium 500 mg 250 mg 100 mg 250 mg 100 mg 25 mg 25 mg 10 mg 5 mg 10 mg 10 mg 1 g 1 g 5 g 1 g C methanol...... D store at: D D store at: D D C Xu 5-P D store at: C Ru-5-P D store at: H solubility C ethanol...... water...... <10% C -Ribulose 1,5-di -Ribo furan -Ribulose 5-phos -Ribulose 1,5-bis -Ribo -Xylulose 5-phos -Ribulose 5-phos 5 5 5 5 5 R0878-100MG R0878-25MG R0878-10MG R7750-5G R7750-1G R7750-250MG R7750-10MG X0754-25MG X0754-5MG R9875-25MG R9875-5MG 83899-100MG 83899-25MG 83899-5MG BioChemika ~90% ≥70% ~90% ≥98% BioChemika H H H H H 2 O...... 50 mg/mL, clear,O...... 50 mg/mL, yellow light 12 9 10 11 9 Na Na O NaO O 11 8 2 2 se 5-phos P FW 230.11 O O B B B B P 8 8 8 2 P ·xH P FW 252.09 P FW 274.07 ·xNa ose 5-phos 2 phos + , ~30%(enzymatic) , O FW 274.07 (Anh) ECNo. 2421407 BRN 4774244 ·yH ≥96% (TLC) phate hydrate disodium salt phate hydratedisodium phate; RuDP phos phate disodium salt phate disodium phate sodium salt phate sodium phate sodium salt phate sodium 2 phate disodium salt phate disodium O FW 310.09 (FA/Anh) [108321-99-9] phate hydrate sodium salt phate hydratesodium [105931-44-0] ≤ 2% ≤ 1% 100 mg 250 mg 100 mg 25 mg 10 mg 10 mg 25 mg 25 mg 25 mg 5 mg 5 mg 5 mg 5 g 1 g PPAR Signaling 29
sigma.com 1 g 5 g 25 g 5 mg 1 mg 10 mg 25 mg α, -gly cer yl-3- cer -gly sn decyl azelaoyl enyl]-3-ethyl- oic acid β2, and 11% for noyl)- propan propan octa thalenyl)carbox- choline; hexa idene)-1-prop idene)-1-prop l-2-yl oxy]-2-methyl β1, 35% for RAR methyl-2-naph cero-3-phos pho cero-3-phos decyl-2-O-(9-carboxy -gly [41859-67-0] [108527-83-9] sn methyl-2H-indo methyl-2H-indo [102121-60-8] = 6.3 µM. AC-93253 has high selectivity; = 6.3 µM. AC-93253 50 . Lipoprotein lipase (LPL) activator. γ. Lipoprotein benz amido)ethyl]phen benz hydro-5,5,8,8-tetra hydro-5,5,8,8-tetra α vs 67% for RAR γ agonist. FW 361.82 FW choline; 1-O-Hexa 4 P FW 651.85 P FW FW 351.44 FW zolium iodide 9 3 E decyl-2-azelaoyl- SI FW 488.43 SI FW B B B7273-1G B7273-5G choline tidyl 2 B7273-25G NO ClNO N NO thia δ, and PPAR α) agonist. EC 66 20 25 25 γ. O...... insoluble H H H H 2 98% (TLC) ≥98% 10 mg/mL in ethanol ≥98% (HPLC) A8843-5MG A6850-1MG A9605-10MG A9605-25MG 33 19 23 22 phos pho phos C of leukemia- studies Retinoid derivative used for gene expression cell line differentiation. (PHL-RAR) acid receptor retinoic The peroxisome proliferator-activated receptor (PPAR) is a member (PPAR) receptor proliferator-activated The peroxisome Bezafibrate is a superfamily. nuclear receptor of the steroid agonist for PPAR receptor proliferator-activated peroxisome PPAR agonists, including Bezafibrate, have beneficial PPARgamma during response of the inflammatory in the suppression effects in the might have clinical efficacy RSV infection and therefore RSV-infection. course of severe solubility DMF...... soluble deionized water...... insoluble RTECS # UE8755000 store at: store Azelaoyl PAF 1-O-Hexa Potent PPAR at: store Bezafibrate 2-[4-[2-(4-Chloro AC-93253 iodide 2-[3-(1,3-Dihydro-1,3,3-tri benzo C H at: store AM580 4-[(5,6,7,8-Tetra amido]benzoic acid C C AC-93253 is a potent, cell permeable, subtype selective RAR AC-93253 is a potent, (RAR solubility pha phos 89% for RAR RAR DMSO...... >12 mg/mL DMSO...... >12
50 5 mg 5 mg lic 20 mg 20 mg g β2 and g is activated by β2) agonist. AC- -n-octyl biphenyl-4-carboxy -n-octyl hydro-3-phenyl-5H-imidazo[1,2- ′ agonist treatment of insulin- g agonist treatment of 7.7 µM for AM-580. 50 lic acid, 4 [59662-49-6] agonist. AC-41848 has high selectivity (92%) γ agonist. AC-41848 has high selectivity (92%) O FW 452.21 (Anh) 452.21 O FW 2 = 5.9 µM. mide hydrate activation in rodents has been shown to increase shown to increase has been g activation in rodents 1. When compared to AM-580 (Prod No A8843), to AM-580 (Prod β1. When compared 50 forms a heterodimeric complex with the retinoid with the retinoid complex a forms a heterodimeric · xH 2 N 2. AC-55649 has high selectivity, 99% for RAR β2. AC-55649 has high selectivity, 2 FW 310.43 FW -Octyl-4-biphenyl carboxy -Octyl-4-biphenyl E E γ. EC ′ 2 nium bro nium bro O BrCl agonists decrease circulationg fatty acid levels and may circulationg g agonists decrease a antidiabetic agents and represent efficacious g agonists are 26 21 O...... >5 mg/mL H H 2 ≥98% (HPLC) ≥98% (HPLC) A9480-5MG A7980-20MG A9480-20MG A7980-5MG 21 21 of 6.9 µM compared to an EC of 6.9 µM compared solubility DMSO...... >7 mg/mL at: store solubility AC-55649 8BCA; 4 DMSO...... ~14 mg/mL H at: store AC-41848 is a potent, cell permeable, subtype selective retinoic AC-41848 is a potent, cell permeable, subtype RAR acid receptor 1-[(2,4-Dichloro phenyl)methyl]-6,7,8,9-tetra 1-[(2,4-Dichloro for RAR AC-41848 hydrate prostaglandins and leukotrienes and regulates the gene expression expression the gene and regulates and leukotrienes prostaglandins is weakly in the storage of fatty acids. PPARß involved of proteins and leukotrienes. Its prostaglandins, activated by fatty acids, not been identified. physiological ligand has PPAR the the Randle glucose levels by invoking affect indirectly thereby carbohydrate and fat metabolism. In Cycle, a pathway that links addition PPAR genes required of expression in decreased rats results resistant This is consistent with PPAR for gluconeogenesis in the liver. into adipose a flux of glucose and fatty acids agonsists promoting of increased muscle with a net result tissue and away from in the gluconeogenesis glucose utilization in muscle and decreased liver. PPAR to as referred novel class of marketed diabetic drugs, collectively the glitazones. X receptor (RXR) to regulate transcription. PPAR to regulate (RXR) X receptor of the number while decreasing the number of small adipocytes insulin adipocytes typically have greater large adipocytes. Smaller glucose and have lower rates of lipolysis take up more sensitivity, to large adipocytes. PPAR compare Similar to other nuclear hormone receptors, peroxisome peroxisome receptors, nuclear hormone Similar to other act as ligand-activated (PPARs) receptors proliferator-activated of storage in the regulation factors that play a role transcription bound to its fatty acid of dietary fats. When and catabolism ligand, PPAR PPAR Signaling PPAR AC-55649 is a subtype selective RAR (RAR 55649 is a potent, orally available isoform selective Retinoic Acid Receptor 31% for RAR 100%. AC-55649 has a potent EC were both isoform receptors acid C a]azepi C 30 PPAR Signaling sigma.com C C (PXR). Theliterature agonist,T0901317(Tularik), hadanEC receptors, itcross-reacted withonlythepregnane Xreceptor orally activeinmice.Whenscreened againstapanelofnuclear Peroxisome proliferator-activated receptor solubility nM and85inthecell-free andcell-basedassays,respectively. based assayswithEC of LXRaandprofiles asafullagonistonhLXRaandhLXRbincell- DMSO...... C oxy]phenyl 3-[3-[N-(2-Chloro-3-tri GW3965 hydrochloride Glaxo Smith Sold forresearch purposesonly, pursuantto anagreement with DMSO...... 20mg/mL solubility High affinity agonistofPPAR- N-(2-Benzoyl phenyl)-O-[2-(methyl-2-pyridinyl amino)ethyl]- GW1929 hydrate store at: 2-[p-(2,2-Dichloro cyclo Ciprofibrate activity ingeneticallyobeseC57B1/6ob/obmice. (±)-5-[4-(1-Methyl cyclo hexyl methoxy)benzyl]thia zol Ciglitizone C GW3965 hasanEC GW3965 isaliverXreceptor fullagonistonhLXRaandhLXRb. agonist (EC Selective peroxisome proliferator-activated receptor-γ (PPAR 13 18 33 30 G6295-25MG G6295-5MG G5668-25MG G5668-5MG C0330-25MG C0330-10MG C3974-5MG ≥98% (HPLC) >98% (HPLC) ≥99% (TLC) H H H H 31 29 14 23 N Cl NO F 3 3 ClNO 2 E O O 3 acetic acid hydrochloride S FW 333.45 4 3 ·xH FW 289.15 50 Kline. 3 ·HClFW 618.51 =3 µM) andantihyperglycemicagentdisplaying 2 O FW 495.57 (Anh) fluoro methyl 50 pro pyl)phen 50 = 125nMinacell-free ligand-sensingassay =190nMand30nM,respectively. Itis [52214-84-3] [74772-77-3] ≥ 20 mg/mL γ oxy]-2-methyl benzyl)-(2,2-diphenyl [405911-17-3] propan α (PPARα) agonist i dine-2,4-dione oic acid ethyl)amino]pro L -tyro sine hydrate γ) 50 25 mg 25 mg 10 mg = 60 5 mg 5 mg 25 mg pyl- 5 mg solubility Glaxo Smith Sold forresearch purposesonlyunderagreement from receptor inhumancells. Potent humanPPAR solubility transfection assays. DMSO...... DMSO...... 26 mg/mL, soluble DMSO...... 26mg/mL, soluble DMSO...... 16mg/mL, C pro 2-(4-(2-(1-Cyclo GW7647 store at: H C GW574716 N’-(4-Diethyl GW4716 store at: H C 2-Chloro-5-nitro-N-phenyl GW9662 H solubility Glaxo Smith Sold forresearch purposesonly, underagreement from connective tissuegrowth factorandactivationofCD36byIL-4. GW9662 isanirreversible PPAR- of exogenousligands.IC receptors thatinteractwithcoactivatorproteins intheabsence The ERRsgenerallyare considered tobeconstitutivelyactive GW4716 isanestrogen-related receptor 29 18 13 G5920-25MG G5920-5MG M6191-25MG M6191-5MG G6793-25MG G6793-5MG ≥98% (HPLC) ≥98% (HPLC) >98% (HPLC) 2 2 2 H H H pionic acid O...... not directly soluble O...... insoluble O...... insoluble 46 21 9 ClN N N 2 3 E E O O 2 O 3 2 S FW 502.75 FW 311.38 3 amino benz FW 276.68 Kline. Kline. hexane α agonist.UsetostudythebiologyofPPARα butyl)-3-cyclo hexyl ureido)ethyl) phenyl thio)-2-methyl- yl idene)-4-hydroxy benzoyl benz amide [95167-41-2] [22978-25-2] 50 [265129-71-3] ≥ valueof300-500nMintransient 14 mg/mL γ antagonist.GW9662inhibits γ (ERR hydra γ) agonist. zide; GSK4716; 25 mg 25 mg 25 mg 5 mg 5 mg 5 mg PPAR Signaling 31
sigma.com α 5 mg 5 mg 1 mg 100 mg 250 mg 500 mg β and RAR- amide lide phenyl)retin phenyl)retin ani [293754-55-9] [65646-68-6] [5300-03-8] [4759-48-2] FW 481.33 FW 9 F 3 FW 391.55 FW 2 FW 300.44 300.44 FW 300.44 FW B B B B 2 2 -Retinoic acid -Retinoic acid (RA) has anti-inflammatory and anti-tumor -Retinoic acid (RA) has NO NSO O O -Retinoic acid -Tretinoin 33 12 28 28 cis cis H H H H cis >98% ≥95% ≥98% (HPLC) ~98% (HPLC) cis T2320-5MG R3255-100MG R3255-250MG R3255-500MG H7779-5MG R4643-1MG 26 17 20 20 LXR agonist whose treatment results in an LXR-dependent up- in an LXR-dependent results LXR agonist whose treatment of ABC1 gene expression regulation mol wt 481.3 activity in cultured Vitamin A acid analogue with antiproliferative induces apoptosis in malignant cancer cells; human breast hemopoietic cell lines. C store at: store Retinoic acid p-hydroxy 4-HPR; N-(4-Hydroxy Fenretinide; at: store T0901317 C at: store 9- 9- at: store 13- Isotretinoin C C receptors. RA attenuates iNOS expression and activity in cytokine- RA attenuates iNOS expression receptors. mitochondrial stimulated murine mesangial cells. It induces swelling and as membrane permeability transition, observed as in membrane potential, and stimulates the release a decrease the apoptosis mechanisms through c implicating of cytochrome and cyclosporin A. by EGTA reversed These activities are pathway. partially via increased expression MMP-1 protein RA also increases transcription. (RAR) and the retinoid receptor acid the retinoic Ligand for both the that act as transcription factors to regulate (RXR) X receptor of normal and malignant cells. and differentiation growth Sealed ampule 13- RAR- is mediated through action. The action of RA 1 g 5 g 5 mg 10 µg 25 µg 50 mg 25 mg 100 mg 500 mg acetic acid oxy poxy]phen oxy)pro oxy)pro EC No. 2061290 BRN 2057223 2061290 BRN EC No. phen [302-79-4] [79558-09-1] [29623-28-7] deca-9Z,11E-dienoic acid deca-9Z,11E-dienoic
-Retinoic acid; Tretinoin; Vitamin A acid -Retinoic acid; Tretinoin; δ) selective agonist. trans −Retinoic acid (ATRA) is a ligand for both the retinoic acid is a ligand for both the retinoic −Retinoic acid (ATRA) FW 300.44 FW FW 402.44 FW FW 296.44 296.44 FW - B B B 2 7 3 all O O O 28 26 32 H H H ≥98% (HPLC) ≥98% (HPLC) ~100 µg/mL in ethanol, ~98% µg/mL ~100 R2625-50MG R2625-100MG R2625-500MG R2625-1G L2167-5MG L2167-25MG R2625-5G H9146-10UG H9146-25UG 20 22 18 C Sealed ampule receptor (RAR) and the retinoid X receptor (RXR). The bound RAR X receptor (RAR) and the retinoid receptor and the growth and RXR act as transcription factors that regulate of both normal and malignant cells. Cytochromes differentiation acid Retinoic of ATRA. P450 (CYPs) catalyze the 4-hydroxylation primes embryonic stem cells to become neurons. all−trans Retinoic acid ATRA; DMSO...... >10 mg/mL at: store 4-[3-(4-Acetyl-3-hydroxy-2-pro pyl 4-[3-(4-Acetyl-3-hydroxy-2-pro L-165,041 store at: store C 13(S)-HODE C 13(S)-Hydroxy octa 13(S)-Hydroxy store at: store β (PPAR PPAR solubility γ agonist PPAR (15-LOX-1) and its main product, of 15-lipoxygenase-1 Expression and esophageal in human colorectal decreased 13(S)-HODE, are anti-inflammatory drugs (NSAIDs) cancers. Certain non-steroidal human colon cancer cells by increased can induce apoptosis in PPAR-delta down-regulates of 15-LOX-1, which expression 13-HODE. through Packaged under Argon. 32 PPAR Signaling sigma.com C for retinoic acidreceptors (RAR) Selective andhighlypotentretinoic acidanalogwithaffinity store at: C thalenyl)-1-prop Arotinoid acid;4-[(E)-2-(5,6,7,8-Tetra TTNPB DMSO...... 20mg/mL solubility pathway. inflammatory andanti-tumoractivity;inducesapoptosisviaap53 PPAR yl)methoxy]benzyl]-2,4-thia zol CS-045; (±)-5-[4-[(6-Hydroxy-2,5,7,8-tetra Troglitazone DMSO...... solubility Packaged undernitrogen. PPARγ PPAR C TTA Tetra genes thatpossessretinoic acidresponsive elements. transcription factors.Produces ligand-activatedtranscriptionof 14 24 24 T3757-25MG T3757-10MG T2573-5MG T1698-5MG >98% (HPLC) ≥97% (NMR) H H H 28 27 29 γ agonist;anti-diabeticthiazolidinedione(TZD)withanti- α agonist;activationinrankingorder: PPAR α >PPAR decyl thio O NO -S-CH 2 B FW 348.48 5 S FW 441.54 2 COOH FW 288.49 Proteinase K,AlkalinePhosphataseandLeupeptin New! Proteomics, andCellCulture To reserveyourcopy, Introducing the and technicalinformationyou need 2000+ enyl]benzoic acid acetic acid LifeScienceWeb Tool Guide New Sigma [71441-28-6] ≥ i Products dine dione 22 mg/mL, soluble 22 mg/mL, Your workisunique...innovative...groundbreaking hydro-5,5,8,8-tetra α, New ® LifeScienceCatalogistheperfect match
β, and methyl chroman-2- supportingGenomics,Functional BioUltraProteins visit γ, whichare nuclear sigma.com/sigmacat1 methyl-2-naph- The New2008-2009 (Available January2008) –lear δ > –risk-fr 25 mg 10 mg n abouttheoptimalonlinetool for fi 5 mg 5 mg ee, high-purityproteins, including store at: DMSO...... 10mg/mL C fluoro 3-[4-(2,4-Bis-tri XCT790 C 4-Chloro-6-(2,3-xylidino)-2-pyrimi dinyl thio WY-14643 biochemical andcell-basedassays.TheIC 10 µM.XCT790inhibitstheconstitutiveactivityofERR nuclear receptors, suchasERR is selective;showingnosignificantantagonistactivityonrelated XCT790 isapotentandspecificinverseagonistofERR solubility ERR withthemSHPpromoter. in transienttransfectionassaysusingGAL4-ERRLBDorfull-length Selective PPAR 23 14 C7081-50MG C7081-10MG X4753-25MG X4753-5MG ≥98% (HPLC) H H 13 14 methyl-1,3,4-thia diazol-2-yl)acryl F ClN 9 N E 4 3 O O 3 2 S FW 596.42 S FW 323.80 fluoro methyl α agonist. Cell Biology, GeneExpression, benzyl [725247-18-7] [50892-23-4] ndingtheproducts oxy)-3-methoxy γ orER amide acetic acid;Pirinixicacid α atconcentrationsbelow 50 valueis300-500nM phenyl]-2-cyano-N-(5-tri- α. XCT790 α inboth 50 mg 10 mg 25 mg 5 mg The shape of Sigma Life Science
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