DOCSLIB.ORG

Supporting Online Material

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Supporting Online Material 1 SUPPLEMENTARY MATERIAL 2 The glycan alphabet is not universal: a hypothesis 3 4 Jaya Srivastava1*, P. Sunthar2 and Petety V. Balaji1 5 6 1Department of Biosciences and Bioengineering, Indian Institute of 7 Technology Bombay, Powai, Mumbai 400076, India 8 9 2Department of Chemical Engineering, Indian Institute of Technology 10 Bombay, Powai, Mumbai 400076, India 11 12 *Corresponding author 13 Email: [email protected] 1 14 CONTENTS Data Description Figure S1 Number of organisms with different number of strains sequenced Figure S2 Biosynthesis pathways Figure S3 Proteome sizes for different number of monosaccharides Figure S4 Prevalence of monosaccharides in species versus that in genomes Figure S5 Bit score distribution plots for hits of various pairs of profiles Table S1 Tools and databases used in this study References References cited in Table S1 Table S2 Comparison of the precursor and nucleotide used for the biosynthesis of two enantiomers of a monosaccharide Flowchart S1 Procedure used to generate HMM profiles Flowchart S2 Precedence rules for assigning annotation to proteins that are hits to two or more profiles and/or BLASTp queries References References to the research articles which describe the pathways (or enzymes of the pathways) of monosaccharide biosynthesis. These formed the basis for generating HMM profiles and choosing BLASTp queries. 15 16 MS-EXCEL file provided separately: Supplementary Data.xlsx 17 Worksheet1 Details of HMM profiles Worksheet2 Details of BLASTp queries Worksheet3 Prevalence of monosaccharides in genomes / species Worksheet4 Abbreviated names of monosaccharides Worksheet5 Enzyme types, enzymes and monosaccharide groups Worksheet6 Precursors of various monosaccharides 18 2 19 Figure S1 The number of species for which different number of strains are sequenced. 20 Six or fewer strains are sequenced for most of the species. On the other hand, more than 21 50 strains are sequenced for 29 species. Escherichia coli and Salmonella enterica have 22 the highest number of sequenced strains (714 and 602, respectively). Genus and species 23 names are not known for 45 endosymbionts; only their host name is known e.g., 24 Legionella endosymbiont. Each such case is considered as a distinct species. 3 4 Mutase Glucose-1-phosphate C1 4 (d)TDP- (d)TDP-fucose C1 ThymidylylT (Pyr to Fur) fucofuranose ) 0 6 4 GPE01130 A GPE09510 3 1 ( C 2 3 - - e @ 1 1 s : : 4 H a C 4 (d)TDP-glucose 1 2 O t 7 F – c 3 7 x u E GPE05430 5 4,6-Dehydratase (R) A 6 0 d e Q Retention of config @ C5 O R - 4 4-AminoT 4 (d)TDP-4-keto-6-deoxy-glucose C1 Eq –NH2@C4 3,4-Ketoisomerase 3,4-Ketoisomerase GPE01830 GPE07510 Eq –OH@C4 Ax –OH@C4 GPE01230 (d)TDP-4-amino- e s (d)TDP-3-keto-6- a (d)TDP-3-keto-6- 4 r 0 0 6-deoxy-glucose C1 3 3 e 4 4 5 4 deoxy-glucose C1 deoxy-galactose C1 m 2 2 i 0 0 3 p E E 2 1 G E GPE01910 9 P P 3-AminoT (E) 3-AminoT (E) 2 - GPE01910 - 1 P G G 1 - F E 5 GPE01230 : 1 5 , Eq –NH @C3 Eq –NH @C3 : T o 2 GPE01230 2 3 3 l ( 0 3 D y ) 4 rm 0 8 W t o 1 -a 0 B C e in y (d)TDP-3-amino-6- 4 X c m lT (d)TDP-3-amino-6- C 9 A m i Q n 4 a 0 4 0 4 T - o C C 3 C deoxy-galactose 1 3 4 ) deoxy-glucose 1 o ( 8 2 @ n 1 (d)TDP-4-keto- 1 2 i 0 0 H E E 1 m AcetylT AcetylT N P L-rhamnose C4 Q6T1W7:1-192 P A – - G Q6TFC6:1-265 G x (3-amino) Q12KT8:1-152 (3-amino) 4 A 4 (d)TDP-Qui4NAc C1 (d)TDP-Qui4NFo E5 ) 4 O F1 4 E - 4 C ( R 6 6 4 4 1 e 62 : (d)TDP-Qui3NAc C1 (d)TDP-Fuc3NAc C1 e A d 5 1- s 4 x u 6: 31 a C 0 – c 1 8 t 3 O t - @ a 2 (d)TDP-4-amino-6- c 3 H s 7 H @ e 0 u 6 d O 0 C (A 4C e – E 4 ) deoxy-galactose 1 P R q - G 4 E AcetylT Q8FBQ3:1-224 4-Epimerase (4-amino) (d)TDP- (d)TDP-6-deoxy- 1 Q2SYH7:1-363 L-rhamnose C4 L-talose 1C 4 4 (d)TDP-Fuc4NAc C1 D-enantiomer L-enantiomer HMM profile BLASTp query D-enantiomer / pyranose form unless mentioned otherwise 25 26 Figure S2a TDP-/dTDP-linked monosaccharides derived from glucose-1-phosphate. 27 Abbreviated names are used for some of the monosaccharides. Full names of these are 28 given in Supplementary_data.xlsx:Worksheet4. 4 29 4 Glucose-1-phosphate C1 GPE00330 CytidylylT 4 CDP-glucose C1 GPE05230 4,6-Dehydratase (R) Retention of config @ C5 GPE40110 C-MeT (E) 3-Epimerase CDP-4-keto-6- CDP-4-keto-3C-methyl- 4C 4C 1 CDP-4-keto-6-deoxy gulose 1 4 GPE02530 deoxy-glucose C1 Eq –Me, Ax-OH@C3 6-deoxy-gulose Ax –OH@C4 4-Reductase GPE06230 4 GPE05630 3-Dehydratase -R e e s E a q d t 4 – u 4 c C O c CDP-6-deoxy gulose C1 u H t CDP-6-deoxy-D3,4-glucocene @ @ a d H GPE06230 s e C e O 4 R – - x P26395:1-330 D3,4-glucocene 4 A Q66DP5:1-329 reductase GPE02530 CDP-3,6-dideoxy-L-glycero- 5-Epimerase glycero 4 CDP-3,6-dideoxy-D- - CDP-cereose C1 CDP-cillose 1C 4 D-glycero-4-hexulose 4 C1 4 D-glycero-4-hexulose C1 GPE06230 4-Reductase 4 e - s R Eq –OH@C4 a E e t 4 q d c C – u u @ O c d H GPE06230 H t 1C e O @ a CDP-L-ascarylose 4 R – C s - x 4 e 4 A 2-Epimerase 4C 4 4C CDP-abequose 1 CDP-paratose C1 CDP-tyvelose 1 P14169:1-338 D-enantiomer / pyranose form unless mentioned otherwise 30 D-enantiomer L-enantiomer HMM profile BLASTp query 31 Figure S2b CDP-linked monosaccharides derived from glucose-1-phosphate. 32 Abbreviated names are used for some of the monosaccharides. Full names of these are 33 given in Supplementary_data.xlsx:Worksheet4. 5 4 Glucose-1-phosphate C1 GPE00430 UridylylT GPE00530 GPE09510 4,6-Dehydratase (R) 4-Epimerase Mutase UDP-galacto- UDP-4-keto-6- 4 4 UDP-glucose C1 UDP-galactose C1 4 Retention of config @ C5 furanose deoxy-glucose C1 GPE02230 (pyranose GPE05510 to furanose) 2 5 3 3 , - ) 4 5 :1 E - - 8 ( R E 6-Dehydrogenase N p 4 T 4 E e Y o C q d im GPE03130 2 n G – u G i @ e 2 P O c GPE03430 0 m H E H t r A N 0 @ a a 0 A – 5 s s A - 7 C e e 4 q 1 4 4C E 0 ( , Decarboxylase 1 E 4 ) UDP-GlcA C1 UDP-4-keto xylose GPE20030 GPE01830 1 4-Epimerase 4-AminoT (A) UDP-4-amino-6- UDP-L-rhamnose C4 GPE01230 GPE02230 Ax –NH @C4 4C 2 deoxy-glucose 1 4 UDP-xylose C1 4C 4 AcetylT UDP-GalA 1 UDP-L-Ara4N C1 (4-amino) 4-Epimerase FormylT GPE02230 GPE50010 Q5UR11:1-213 (4-amino) 4C 4 UDP-L-arabinose 1 UDP-L-Ara4NFo UDP-Qui4NAc C1 4 C1 D-enantiomer L-enantiomer HMM profile BLASTp query D-enantiomer / pyranose form unless mentioned otherwise 34 35 Figure S2c UDP-linked monosaccharides derived from glucose-1-phosphate. 36 Abbreviated names are used for some of the monosaccharides. Full names of these are 37 given in Supplementary_data.xlsx:Worksheet4. 6 GPE01330 4 Fructofuranose-6-phosphate Glucosamine-6-phosphate C1 GPE07030 2-AmidoT GPE07130 M lT GPE07230 y u Isomease t 0 G t e 3 P a GPE07330 1 G E c 8 P 0 s A 0 E 9 e Q5SIM4:1-254 E 0 1 P 9 3 G 6 P29954:1-387 3 0 0 1 4C C4 Mannose-6-phosphate 1 GDP-L-galactose GPE09230 4 3,5 Glc2NAc-6-phosphate Glucosamine-1-phosphate C1 -e GPE09330 Mutase 4C R p 1 4N im GPE09630 RR er AcetylT 5: as 1-3 e 4 Mutase GPE08510 50 Mannose-1-phosphate C1 (2-amino) GPE09430 GPE00620 (GlmU-CTD) GPE00720 GuanylylT 4 Glc2NAc-1-phosphate C1 4 6-dehydrogenase 4 GDP-ManA C1 GDP-mannose C1 GPE03210 GPE00831 GPE03430 GPE05020 4,6-dehydratase (R) UridylylT UridylylT Retention of config @ C5 GPE00830 (GlmU-NTD) 4-AminoT (E) 4 4 C1 GDP-Per C1 GDP-4-keto-6-deoxy mannose 4 Eq –NH2@C4 UDP-Glc2NAc C1 AcetylT Q7DBF7:1-221 GPE01430 Eq 4- –OH O85353:1-215 se 3,5-epimerase, red @C (4-amino) ta uct 4 ra GP ase d 4-reductase (A) 4 E06 (E 4C hy 0 -r 51 ) GDP-Per4Ac 1 e 63 GPE06030 Ax –OH@C4 ed 0 d 05 A u 3- E x – ct GP O as H@ e 1C C4 (A 4 GDP-L-fucose 4 ) GDP-rhamnose C1 GDP-4-keto-3,6- 4 4C dideoxy mannose C1 GDP-6-deoxy-talose 1 5-epimerase, 4-reductase (A) GPE06030 Ax –OH@C4 1 GDP-L-colitose C4 D-enantiomer L-enantiomer HMM profile BLASTp query D-enantiomer / pyranose form unless mentioned otherwise 38 39 Figure S2d GDP- and UDP-linked monosaccharides derived from fructofuranose-6- 40 phosphate.
Load more

Recommended publications
  • Converting Galactose Into the Rare Sugar Talose with Cellobiose 2-Epimerase As Biocatalyst
    molecules Article Converting Galactose into the Rare Sugar Talose with Cellobiose 2-Epimerase as Biocatalyst Stevie Van Overtveldt, Ophelia Gevaert, Martijn Cherlet, Koen Beerens and Tom Desmet * Centre for Synthetic Biology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Gent, Belgium; [email protected] (S.V.O.); [email protected] (O.G.); [email protected] (M.C.); [email protected] (K.B.) * Correspondence: [email protected]; Tel.: +32-9264-9920 Academic Editors: Giorgia Oliviero and Nicola Borbone Received: 17 September 2018; Accepted: 29 September 2018; Published: 1 October 2018 Abstract: Cellobiose 2-epimerase from Rhodothermus marinus (RmCE) reversibly converts a glucose residue to a mannose residue at the reducing end of β-1,4-linked oligosaccharides. In this study, the monosaccharide specificity of RmCE has been mapped and the synthesis of D-talose from D-galactose was discovered, a reaction not yet known to occur in nature. Moreover, the conversion is industrially relevant, as talose and its derivatives have been reported to possess important antimicrobial and anti-inflammatory properties. As the enzyme also catalyzes the keto-aldo isomerization of galactose to tagatose as a minor side reaction, the purity of talose was found to decrease over time. After process optimization, 23 g/L of talose could be obtained with a product purity of 86% and a yield of 8.5% (starting from 4 g (24 mmol) of galactose). However, higher purities and concentrations can be reached by decreasing and increasing the reaction time, respectively. In addition, two engineering attempts have also been performed.
    [Show full text]
  • Screening of Candidate Substrates and Coupling Ions of Transporters By
    TOOLS AND RESOURCES Screening of candidate substrates and coupling ions of transporters by thermostability shift assays Homa Majd1†, Martin S King1†, Shane M Palmer1, Anthony C Smith1, Liam DH Elbourne2, Ian T Paulsen2, David Sharples3,4, Peter JF Henderson3,4, Edmund RS Kunji1* 1Medical Research Council Mitochondrial Biology Unit, University of Cambridge, Cambridge, United Kingdom; 2Department of Molecular Sciences, Macquarie University, Sydney, Australia; 3Astbury Centre for Structural Molecular Biology, University of Leeds, Leeds, United Kingdom; 4School of Biomedical Sciences, University of Leeds, Leeds, United Kingdom Abstract Substrates of most transport proteins have not been identified, limiting our understanding of their role in physiology and disease. Traditional identification methods use transport assays with radioactive compounds, but they are technically challenging and many compounds are unavailable in radioactive form or are prohibitively expensive, precluding large- scale trials. Here, we present a high-throughput screening method that can identify candidate substrates from libraries of unlabeled compounds. The assay is based on the principle that transport proteins recognize substrates through specific interactions, which lead to enhanced stabilization of the transporter population in thermostability shift assays. Representatives of three different transporter (super)families were tested, which differ in structure as well as transport and ion coupling mechanisms. In each case, the substrates were identified correctly from a large set of *For correspondence: chemically related compounds, including stereo-isoforms. In some cases, stabilization by substrate [email protected] binding was enhanced further by ions, providing testable hypotheses on energy coupling †These authors contributed mechanisms. equally to this work DOI: https://doi.org/10.7554/eLife.38821.001 Competing interests: The authors declare that no competing interests exist.
    [Show full text]
  • 25 05.Html.Ppt [Read-Only]
    25.5 A Mnemonic for Carbohydrate Configurations The Eight D-Aldohexoses CH O H OH CH2OH The Eight D-Aldohexoses All CH O Altruists Gladly Make Gum In H OH Gallon CH2OH Tanks The Eight D-Aldohexoses All Allose CH O Altruists Altrose Gladly Glucose Make Mannose Gum Gulose In Idose H OH Gallon Galactose CH2OH Tanks Talose The Eight D-Aldohexoses Allose CH O Altrose Glucose Mannose Gulose Idose H OH Galactose CH2OH Talose The Eight D-Aldohexoses Allose CH O Altrose Glucose Mannose Gulose H OH Idose H OH Galactose CH2OH Talose The Eight D-Aldohexoses Allose CH O Altrose Glucose Mannose Gulose HO H Idose H OH Galactose CH2OH Talose The Eight D-Aldohexoses Allose CH O Altrose Glucose Mannose Gulose H OH Idose H OH Galactose CH2OH Talose The Eight D-Aldohexoses Allose CH O Altrose Glucose Mannose H OH Gulose H OH Idose H OH Galactose CH2OH Talose The Eight D-Aldohexoses Allose CH O Altrose Glucose Mannose HO H Gulose H OH Idose H OH Galactose CH2OH Talose The Eight D-Aldohexoses Allose CH O Altrose Glucose Mannose Gulose HO H Idose H OH Galactose CH2OH Talose The Eight D-Aldohexoses Allose CH O Altrose Glucose Mannose H OH Gulose HO H Idose H OH Galactose CH2OH Talose The Eight D-Aldohexoses Allose CH O Altrose Glucose Mannose HO H Gulose HO H Idose H OH Galactose CH2OH Talose The Eight D-Aldohexoses Allose CH O Altrose Glucose Mannose H OH Gulose H OH Idose H OH Galactose CH2OH Talose The Eight D-Aldohexoses Allose CH O Altrose Glucose H OH Mannose H OH Gulose H OH Idose H OH Galactose CH2OH Talose The Eight D-Aldohexoses Allose CH O Altrose
    [Show full text]
  • Reduced Calorie D-Aldohexose Monosaccharides
    Europaisches Patentamt 19 European Patent Office Office europeen des brevets © Publication number: 0 478 580 B1 12 EUROPEAN PATENT SPECIFICATION @ Date of publication of patent specification © int. ci.5: A23L 1/236, C13K 13/00 06.10.93 Bulletin 93/40 (2j) Application number : 90908336.2 (22) Date of filing : 07.05.90 (86) International application number : PCT/US90/02534 (87) International publication number : WO 90/15545 27.12.90 Gazette 90/29 (54) REDUCED CALORIE D-ALDOHEXOSE MONOSACCHARIDES. (30) Priority : 22.06.89 US 369985 (73) Proprietor: UOP 25 East Algonquin Road Des Plaines, Illinois 60017-5017 (US) (43) Date of publication of application 08.04.92 Bulletin 92/15 (72) Inventor : ARENA, Blaise, J. 621 Parsons © Publication of the grant of the patent : Des Plaines, IL 60016 (US) 06.10.93 Bulletin 93/40 Inventor : ARNOLD, Edward, C. 941 East Hillside Naperville, IL 60540 (US) @ Designated Contracting States : AT BE CH DE DK ES FR GB IT LI LU NL SE (74) Representative : Brock, Peter William U RQU HART-DYKES & LORD 91 Wimpole References cited : Street EP-A- 257 626 London W1M 8AH (GB) US-A- 3 667 969 US-A- 4 262 032 JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE vol.21, December 1970, BARK- ING, GB, pages 650-653; "Organoleptic effect in sugar structures", see the whole document CO o 00 If) 00 Note : Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted.
    [Show full text]
  • Note Solubility of D-Galactose, D-Talose, and D-Tagatose In
    _ Food Science and Technology Research, 21 (6), 801 803, 2015 Copyright © 2015, Japanese Society for Food Science and Technology doi: 10.3136/fstr.21.801 http://www.jsfst.or.jp Note Solubility of D-Galactose, D-Talose, and D-Tagatose in Aqueous Ethanol at Low Temperature * Da-Ming GAO, Takashi KOBAYASHI and Shuji ADACHI Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan Received June 14, 2015 ; Accepted August 20, 2015 _ The solubility of D-galactose, D-tagatose, and D-talose in aqueous ethanol (20 80 wt%) was measured in _ the temperature range of 30℃ to 20℃. The solubility of each sugar decreased upon increasing the ethanol concentration and decreasing the temperature. The solubility of D-talose and D-tagatose was higher than that of D-galactose under all conditions. The temperature dependence of the solubility of each hexose can be expressed by the van’t Hoff equation. The dissolution enthalpy of each hexose decreased upon increasing the ethanol concentration. The dissolution enthalpy of D-talose was higher than that of D-galactose and D-tagatose. Keywords: D-galactose, D-talose, D-tagatose, solubility, aqueous ethanol Introduction Therefore, to reduce the load on the separation process, decreasing D-Tagatose and D-talose, both of which are rare sugars, have the temperature or increasing the ethanol concentration for many important uses such as food additives to improve health and precipitating desirable or undesirable components before extend life span (Levin et al., 1995; Lu et al., 2008) and raw chromatographic separation is considered a possible solution as the materials to synthesize value-added products (Baer, 1962; Yu and first step in the purification process.
    [Show full text]
  • D-TAGATOSE Chemical and Technical Assessment (CTA) First Draft Prepared by Yoko Kawamura, Xxx
    Chemical and Technical Assessment 61st JECFA D-TAGATOSE Chemical and Technical Assessment (CTA) First draft prepared by Yoko Kawamura, xxx ©FAO 2004 1 Summary D-Tagatose is a ketohexose, an epimer of D-fructose isomerised at C-4. It was identified as a component of a gum exudate of the cacao tree (Sterculia setigera) and also detected as a component of an oligosaccharide in lichens of the Rocella species. In the bacterial metabolism of lactose, it may be formed from D-galactose by enzymatic isomerization catalyzed by L-arabinose isomerase under alkaline conditions in the presence of calcium. It is as virtually odourless, white or almost white, non-hygroscopic crystals and it has almost same sweetness as sucrose and less than half the calories of sucrose. Functional uses of D-tagatose as food additives are used as sweetener, texturizer, stabilizer, humectant, and formulation aid. D-Tagatose was evaluated at 55th JECFA (2000), but an ADI could not be allocated. At 57th JECFA (2001) an ADI of 0-80 mg/kg bw was established. Current JECFA specifications for D-tagatose were prepared at the 55th JECFA (2001), maintained at 57th JECFA and published in FNP 52 Add 9 (2001). In the light of additional toxicological data, an ADI and specifications were reviewed at 61st JECFA (2003) and they were maintained. 2 Description D-Tagatose occurs as virtually odorless, white or almost white, non-hygroscopic crystals and it has almost same sweetness as sucrose. 3 Manufacturing 3.1 Raw materials Lactose (food-grade), hydrochloric acid (food-grade), calcium hydroxide (technical-grade), sulfuric acid (technical-grade), immobilized lactase, ion exchange resins 3.2 Method of manufacture D-Tagatose is produced from lactose in a two-step process.
    [Show full text]
  • Characterization of a Thermotolerant ROK-Type Mannofructokinase from Streptococcus Mitis: Application to the Synthesis of Phosphorylated Sugars
    Characterization of a thermotolerant ROK-type mannofructokinase from Streptococcus mitis: application to the synthesis of phosphorylated sugars Carine Vergne-Vaxelaire, Aline Mariage, Jean-Louis Petit, Aurélie Fossey-Jouenne, Christine Guérard-Hélaine, Ekaterina Darii, Adrien Debard, Stessy Nepert, Virginie Pellouin, Marielle Lemaire, et al. To cite this version: Carine Vergne-Vaxelaire, Aline Mariage, Jean-Louis Petit, Aurélie Fossey-Jouenne, Christine Guérard- Hélaine, et al.. Characterization of a thermotolerant ROK-type mannofructokinase from Streptococcus mitis: application to the synthesis of phosphorylated sugars. Applied Microbiology and Biotechnology, Springer Verlag, 2018, 102 (13), pp.5569-5583. 10.1007/s00253-018-9018-1. hal-02323767 HAL Id: hal-02323767 https://hal.archives-ouvertes.fr/hal-02323767 Submitted on 22 Oct 2019 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. 24/04/2018 e.Proofing Characterization of a thermotolerant ROK-type mannofructokinase from Streptococcus mitis: application to the synthesis of phosphorylated sugars
    [Show full text]
  • CHEM 331 Problem Set #6- Lehninger 5E, Chapter 7 Due Wednesday, November14, 2012 ANSWER KEY (56 Total Pts.) 1. in the Monosaccha
    CHEM 331 Problem Set #6- Lehninger 5e, Chapter 7 Due Wednesday, November14, 2012 ANSWER KEY (56 total pts.) 1. In the monosaccharide derivatives known as sugar alcohols, the carbonyl oxygen is reduced to a hydroxyl group. For example, D-glyceraldehyde can be reduced to glycerol. However, this sugar alcohol is no longer designated D or L. Why? (2 pts.) With reduction of the carbonyl oxygen to a hydroxyl group, the stereochemistry at C-1 and C-3 is the same; the glycerol molecule is not chiral. 2. Many carbohydrates react with phenyl-hydrazine (C6H5NHNH2) to form bright yellow crystalline derivatives known as osazones: The melting temperatures of these derivatives are easily determined and are characteristic for each osazone. This information was used to help identify monosaccharides before the development of HPLC or gas-liquid chromatography. Listed below are the melting points (MPs) of some aldose-osazone derivatives: As the table shows, certain pairs of derivatives have the same melting points, although the underivatized monosaccharides do not. Why do glucose and mannose, and similarly galactose and talose, form osazone derivatives with the same melting points? (3 pts.) The configuration at C-2 of an aldose is lost in its osazone derivative, so aldoses dif- fering only at the C-2 configuration (C-2 epimers) give the same derivative, with the same melting point. Glucose and mannose are C-2 epimers and thus form the same osazone; the same is true for galactose and talose (see Fig. 7–3). 3. Describe the common structural features and the differences for each pair: (a) cellulose and glycogen; (b) D-glucose and D-fructose; (c) maltose and sucrose.
    [Show full text]
  • Introduction (Pdf)
    Dictionary of Natural Products on CD-ROM This introduction screen gives access to (a) a general introduction to the scope and content of DNP on CD-ROM, followed by (b) an extensive review of the different types of natural product and the way in which they are organised and categorised in DNP. You may access the section of your choice by clicking on the appropriate line below, or you may scroll through the text forwards or backwards from any point. Introduction to the DNP database page 3 Data presentation and organisation 3 Derivatives and variants 3 Chemical names and synonyms 4 CAS Registry Numbers 6 Diagrams 7 Stereochemical conventions 7 Molecular formula and molecular weight 8 Source 9 Importance/use 9 Type of Compound 9 Physical Data 9 Hazard and toxicity information 10 Bibliographic References 11 Journal abbreviations 12 Entry under review 12 Description of Natural Product Structures 13 Aliphatic natural products 15 Semiochemicals 15 Lipids 22 Polyketides 29 Carbohydrates 35 Oxygen heterocycles 44 Simple aromatic natural products 45 Benzofuranoids 48 Benzopyranoids 49 1 Flavonoids page 51 Tannins 60 Lignans 64 Polycyclic aromatic natural products 68 Terpenoids 72 Monoterpenoids 73 Sesquiterpenoids 77 Diterpenoids 101 Sesterterpenoids 118 Triterpenoids 121 Tetraterpenoids 131 Miscellaneous terpenoids 133 Meroterpenoids 133 Steroids 135 The sterols 140 Aminoacids and peptides 148 Aminoacids 148 Peptides 150 β-Lactams 151 Glycopeptides 153 Alkaloids 154 Alkaloids derived from ornithine 154 Alkaloids derived from lysine 156 Alkaloids
    [Show full text]
  • The Carbohydrates
    Title The Carbohydrates [C(H2O)]n Emil Hermann Fischer (1852-1919) F-R Convention The Fischer-Rosanoff Convention CHO CHO CHO H OH H OH C2-OH H OH H OH C3-OH H OH H OH C4-OH H OH H OH C5-OH CH2OH CH2OH C6-CH2OH Fischer Projections Rosanoff Modification D/L Series Fischer-Rosanoff D- and L-Series OH on the right of the highest OH on the left of the highest numbered chiral carbon = D-series. numbered chiral carbon = L-series. D-Aldohexoses The D-Aldohexoses C5 8 right C3 2 right 2 left 2 right 2 left C4 4 right 4 left C2 right left right left right left right left Allose Glucose Gulose Galactose Altrose Mannose Idose Talose All altruists gladly make gum in gallon tanks [L. Fieser] Rxn of Aldoses Reactions of Aldoses CHO =N-NHPh CHO HO OH 3 equiv. PhNHNH2 =N-NHPh 3 equiv. PhNHNH2 OH OH OH OH OH HNO3 OH HNO3 OH OH OH osazone NaBH4 NaBH4 CH2OH CH2OH CH2OH Br2/H2O + PhNH2 + NH3 Br2/H2O CO2H CH2OH CO2H CO2H CH2OH CO2H OH OH OH HO HO HO OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH CH2OH CH2OH CO2H CO2H CH2OH CH2OH aldonic acid alditol aldaric acid aldaric acid alditol aldonic acid achiral achiral Osazones More on Osazones CHO CH2OH CHO O Ca(OH)2 OH Ca(OH)2 HO HO HO HO OH OH OH (Lobry de Bruyn- OH OH Alberda van Eckenstein OH rearrangement, 1895) CH2OH CH2OH CH2OH D-glucose D-fructose D-mannose 1 equiv.
    [Show full text]
  • Principles of Chemical Nomenclature a GUIDE to IUPAC RECOMMENDATIONS Principles of Chemical Nomenclature a GUIDE to IUPAC RECOMMENDATIONS
    Principles of Chemical Nomenclature A GUIDE TO IUPAC RECOMMENDATIONS Principles of Chemical Nomenclature A GUIDE TO IUPAC RECOMMENDATIONS G.J. LEIGH OBE TheSchool of Chemistry, Physics and Environmental Science, University of Sussex, Brighton, UK H.A. FAVRE Université de Montréal Montréal, Canada W.V. METANOMSKI Chemical Abstracts Service Columbus, Ohio, USA Edited by G.J. Leigh b Blackwell Science © 1998 by DISTRIBUTORS BlackweilScience Ltd Marston Book Services Ltd Editorial Offices: P0 Box 269 Osney Mead, Oxford 0X2 0EL Abingdon 25 John Street, London WC1N 2BL Oxon 0X14 4YN 23 Ainslie Place, Edinburgh EH3 6AJ (Orders:Tel:01235 465500 350 Main Street, Maiden Fax: MA 02 148-5018, USA 01235 465555) 54 University Street, Carlton USA Victoria 3053, Australia BlackwellScience, Inc. 10, Rue Casmir Delavigne Commerce Place 75006 Paris, France 350 Main Street Malden, MA 02 148-5018 Other Editorial Offices: (Orders:Tel:800 759 6102 Blackwell Wissenschafts-Verlag GmbH 781 388 8250 KurfUrstendamm 57 Fax:781 388 8255) 10707 Berlin, Germany Canada Blackwell Science KK Copp Clark Professional MG Kodenmacho Building 200Adelaide St West, 3rd Floor 7—10 Kodenmacho Nihombashi Toronto, Ontario M5H 1W7 Chuo-ku, Tokyo 104, Japan (Orders:Tel:416 597-1616 800 815-9417 All rights reserved. No part of Fax:416 597-1617) this publication may be reproduced, stored in a retrieval system, or Australia BlackwellScience Pty Ltd transmitted, in any form or by any 54 University Street means, electronic, mechanical, Carlton, Victoria 3053 photocopying, recording or otherwise, (Orders:Tel:39347 0300 except as permitted by the UK Fax:3 9347 5001) Copyright, Designs and Patents Act 1988, without the prior permission of the copyright owner.
    [Show full text]
  • Racemic Carbohydrates – Fact Or Fiction?
    Special Issue Reviews and Accounts ARKIVOC 2007 (ii) 266-271 Racemic carbohydrates – fact or fiction? Alexander Senning Department of Chemistry, Building 207, Technical University of Denmark, DK-2800 Kgs. Lyngby, Denmark E-mail: [email protected] Abstract Chemical Abstracts Service has developed unsound practices in the naming and handling of simple carbohydrates such as aldopentoses 1, aldohexoses 2, and ketohexoses 3. Typically, the common name glucose is sometimes, inappropriately, interpreted as meaning DL-glucose DL-2d. Thus, a considerable number of CA names and registry numbers have been created for non- existing racemic carbohydrates and linked to irrelevant references which, moreover, in many cases cannot be retrieved by the SciFinder Scholar program. Keywords: Aldohexoses, aldopentoses, carbohydrates, chemical abstracts, 2-ketohexoses, racemates, registry numbers Introduction Off hand it is easy to dismiss racemic carbohydrates such as DL-glucose DL-2d or DL-ribose DL- 1c as most unlikely objects of chemical endeavor − the non-enantiospecific or partially non- enantiospecific stepwise construction of, say, pentoses or hexoses will never lead to racemates, but rather to complicated diastereomeric mixtures. Should a preexisting single carbohydrate stereoisomer be subjected to non-stereospecific chain elongation a mixture of anomers, but never a racemate, would be produced. As far as theoretical chemistry is concerned it is hard to imagine an uncharted property of a racemic carbohydrate worth the computational effort. Finally, biological studies of racemic carbohydrates would add nothing to the already extensive knowledge of the natural enantiomers and their unnatural counterparts. For accounts of organic stereochemistry in general, cf. Ref.,1 for the systematics and stereochemistry of the common monosaccharides, cf.
    [Show full text]