Promoted More Effectively by D-Allose Than by Glucose (Regulation/Malonate/Cyclohexlmide/Mannose) DONNA B

Total Page:16

File Type:pdf, Size:1020Kb

Promoted More Effectively by D-Allose Than by Glucose (Regulation/Malonate/Cyclohexlmide/Mannose) DONNA B Proc. Natl. Acad. Sci. USA Vol. 83, pp. 5858-5860, August 1986 Biochemistry Hexose transport control in a fibroblast metabolic mutant can be promoted more effectively by D-allose than by glucose (regulation/malonate/cyclohexlmide/mannose) DONNA B. ULLREY AND HERMAN M. KALCKAR Unit of Biochemistry in the Department of Chemistry, Boston University, Boston, MA 02215 Contributed by Herman M. Kalckar, April 28, 1986 ABSTRACT By studying the energy-requiring control of transport system (4), was able to induce a well-expressed the hexose transport system (the transport "curb") in a lung transport curb in various types of fibroblasts (5, 6, *). In the fibroblast mutant called the phosphoglucose isomerase mutant PGI mutant that is unable to respond to mannose or D- (because it is devoid of the enzyme phosphoglucose isomerase) glucosamine, D-allose turns out to develop a curb that, much the following features were noted. The aldohexose D-allose, if like glucose, is abolished by malonate. In the parental line, added over 20 hr to a culture of the mutant, promotes the 023, in which several D-aldohexoses are able to develop a development of an intense curb ofthe hexose transport system, hexose transport curb (1), D-allose also brings about a greatly surpassing that brought about by incubation with pronounced transport curb, which also seems to be energy glucose. The allose-mediated curb can be circumvented by requiring. As will be discussed in this paper, D-allose, in various metabolic inhibitors as well as by the presence of other amounts as low as 1 mM, exerts a highly pronounced curb in aldohexoses such as mannose. the PGI mutant surpassing that brought about by glucose. A regulatory energy-requiring system that we have called the hexose transport "curb" has been examined in a cultured MATERIALS AND METHODS hamster fibroblast mutant, DS7, devoid of the enzyme phosphoglucose isomerase (D-glucose-6-phosphate ketol- Cells used were a Chinese hamster lung fibroblast line lacking isomerase, EC 5.3.1.9) (the PGI mutant). The parental line of PGI (DS7) and its parental line (023) (see ref. 6). Both were the mutant, 023, uses glucose readily for energy metabolism. tested by the 4',6-diamidino-2-phenylindole stain method and The transport curb in 023 is promoted by feeding with glucose were found free of mycoplasma (D. V. Young, Bioassay as well as with mannose or D-glucosamine. In DS7, the PGI Systems Research Corp.). The cells were grown in Dulbec- mutant, the two latter hexoses can be used in energy co's modified Eagle's medium (DMEM) with 10% fetal metabolism, yet no transport curb ensues. Conversely, bovine serum. Before the uptake test the cells were rinsed glucose, unable to serve in energfymetabolism ofthis mutant, twice with sugar-free DMEM; the cells were then given remains a promoter of the curb of its transport system. The modified DMEM without pyruvate and with various sugars all-cis aldohexose D-allose has turned out to be the most replacing glucose and supplemented with 10% dialyzed fetal effective promoter of the hexose transport curb. This curb bovine serum (Sigma) for 16-20 hr. Chx (Sigma) was used at can be released by various metabolic inhibitors, such as 35 gM (7). Other additions are indicated for the individual malonate or cycloheximide (Chx). Addition of mannose in experiments. Sugars and malonate were obtained from Sig- excess will also prevent the allose-induced transport curb in ma. the PGI mutant. 3-O-Methylglucose Transport. Cultures were rinsed three A comparison of the down-regulatory patterns of the times with sugar-free and serum-free medium. They were hexose transport system, which we call the "mediated curb," then preloaded with 50 mM 3-O-methylglucose in DMEM between a fibroblast mutant, defective in PGI (the PGI without glucose or serum for 30 min at 370C. The cells were mutant), and its parental line shows the following differences. next rinsed rapidly with 10 ml of phosphate-buffered saline In the parental line, like fibroblast cultures from other (PBS) and then incubated 20 sec at 220C with 3-0- hamster lines (tumorigenic or not), glucose and other ['4C]methylglucose containing L-[3H]glucose to check for aldohexoses, such as D-glucosamine or D-mannose, "in- completeness of washing. After the transport test the cells duce" a marked curb of their own transport system (1, 2). were rinsed rapidly with ice-cold PBS. In some experiments Cultures deprived of sugars or fed fructose instead of D- the cold PBS contained 0.1 mM phloretin. The cells were aldohexose consistently showed much higher rates ofhexose extracted with ethanol and the extracts were assayed for transport (1). radioactivity in a scintillation counter. The results were The transport curb is energy-requiring and it also depends expressed as pmol/mg of cell protein per 20 sec (from on protein synthesis, since the curb is released by inhibitors duplicate samples). of oxidative phosphorylation as well as by inhibitors of Galactose Uptake Test. Cultures were rinsed three times protein synthesis (1-3). with PBS at 370C, incubated 5 or 10 min at 370C with 0.1 mM The D-aldohexoses that can induce a transport curb in the [14C]galactose, rinsed, and analyzed as described (2, 7). The PGI mutant are much more restricted. Neither D-glUCOS- results are expressed as nmol/mg of cell protein per 5 or 10 amine nor mannose was able to elicit a transport curb; only in the tables. Radiochemicals were glucose or galactose has retained this ability (1, 2). min, as stated respective Surprisingly enough, the all-cis hexose D-allose, suppos- from New England Nuclear. edly a nonmetabolizable hexose, albeit a ligand ofthe hexose Abbreviations: Chx, cycloheximide; PGI, phosphoglucose isomer- ase. The publication costs of this article were defrayed in part by page charge *Ullrey, D. B. & Kalckar, H. M. (1986) 86th Meeting of the payment. This article must therefore be hereby marked "advertisement" American Society of Microbiology, March 23-28, 1986, abstr. in accordance with 18 U.S.C. §1734 solely to indicate this fact. K195, p. 226. 5858 Downloaded by guest on September 23, 2021 Biochemistry: Ullrey and Kalckar Proc. Natl. Acad. Sci. USA 83 (1986) 5859 Table 1. Regulation of hexose uptake in 023 and DS7 cultures Table 3. Glucose and allose curb of hexose transport in the PGI mutant nmol/mg of protein per 10 min 3-O-[14C]Methylglucose transport, Sugar DS7 023 Sugar pmol/mg of protein per 20 sec Ratio Fructose (22 mM) 5.34 4.79 First incubation (18 hr) D-Glucosamine (5 mM) 4.36 2.12 None 35.94 Glucose (22 mM) 1.81 2.25 Fructose (22 mM) 47.62 Allose (22 mM) 1.06 1.30 Glucose (22 mM) 13.36 Allose (22 mM) 8.34 Near-confluent cultures were fed various hexoses with 10% Allose (5 mM) 8.18 dialyzed fetal calf serum over 20 hr. Uptake tests were performed Second incubation (7 hr)* with 0.1 mM [U-_4C]galactose at 370C for 10 min. Fructose (22 mM) 45.95 1.02 + Chx 47.06 RESULTS AND DISCUSSION Glucose (22 mM) 20.51 + Chx 55.00 2.68 Table 1 indicates that allose elicits an even stronger transport Allose (22 mM) 17.39 2.62 curb than glucose in the PGI mutant and the parental strain. + Chx 45.63 The fact that the allose-induced transport curb is released by Confluent DS7 cultures were maintained for 18 hr in sugar-free malonate (Table 2) indicates that this is a true curb and not medium containing L-glutamine and supplemented with 10% dialyzed simple toxicity. This is supported by the prevention of the fetal calf serum. Subsequently, 22 mM hexoses were added with or establishment of the allose-induced curb by Chx (Table 3). without 35 uM Chx; this refeeding period spanned only 7 hr. Confluent DS7 cultures were incubated for 18 hr in growth Transport tests were then carried out with 0.01 mM 3-0-[14C]- medium containing fructose, glucose, allose, or no sugar. The methylglucose for 20 sec at 23°C. sugar concentrations were 22 mM; however, an extra pair of *Sugar and 35 ,M Chx were added to original sugar-free samples for allose incubation mixtures with only 5 mM of this sugar was 7 hr. added (Table 3, top). A second set of hexose-starved DS7 cultures was exposed to Chx (35 gM) over 7 hr in the It should be emphasized here that the intense transport presence of 22 mM fructose, glucose, or allose and then curb that develops after 20 hr of exposure to D-allose is not analyzed. It can be seen in Table 3, bottom, that Chx is able a plain toxic action by this sugar but a regulatory effect. This to forestall the onset of the hexose transport curb, including appears from the fact that the additional presence of meta- that elicited by allose. bolic inhibitors over the same extended span of time still Table 4 illustrates the competition between allose and permitted the culture to manifest unbridled transport, as mannose. Since this mutant catabolizes mannose rapidly (1, determined in the transport test. 2), a large excess of this sugar was used. In the presence of In general, the biochemical literature on D-allose seems 22 mM mannose, allose fails to elicit a transport curb. The rather sparse. In an important study about 10 years ago (4) it lactic acid generated per mg of cell protein over 18 hr was found that D-allose (3H-labeled) acts as a transport ligand amounted to 3.7-4.3 ,umol from pyruvate and an additional in the hexose transport system ofadipose fat cells.
Recommended publications
  • Electronic Supplementary Information
    Electronic Supplementary Material (ESI) for Chemical Science. This journal is © The Royal Society of Chemistry 2019 Electronic Supplementary Information Poly(ionic liquid)s as a Distinct Receptor Material to Create Highly- Integrated Sensing Platform for Efficiently Identifying a Myriad of Saccharides Wanlin Zhang, Yao Li, Yun Liang, Ning Gao, Chengcheng Liu, Shiqiang Wang, Xianpeng Yin, and Guangtao Li* *Corresponding authors: Guangtao Li ([email protected]) S1 Contents 1. Experimental Section (Page S4-S6) Materials and Characterization (Page S4) Experimental Details (Page S4-S6) 2. Figures and Tables (Page S7-S40) Fig. S1 SEM image of silica colloidal crystal spheres and PIL inverse opal spheres. (Page S7) Fig. S2 Adsorption isotherm of PIL inverse opal. (Page S7) Fig. S3 Dynamic mechanical analysis and thermal gravimetric analysis of PIL materials. (Page S7) Fig. S4 Chemical structures of 23 saccharides. (Page S8) Fig. S5 The counteranion exchange of PIL photonic spheres from Br- to DCA. (Page S9) Fig. S6 Reflection and emission spectra of spheres for saccharides. (Page S9) Table S1 The jack-knifed classification on single-sphere array for 23 saccharides. (Page S10) Fig. S7 Lower detection concentration at 10 mM of the single-sphere array. (Page S11) Fig. S8 Lower detection concentration at 1 mM of the single-sphere array. (Page S12) Fig. S9 PIL sphere exhibiting great pH robustness within the biological pH range. (Page S12) Fig. S10 Exploring the tolerance of PIL spheres to different conditions. (Page S13) Fig. S11 Exploring the reusability of PIL spheres. (Page S14) Fig. S12 Responses of spheres to sugar alcohols. (Page S15) Fig.
    [Show full text]
  • WO 2013/070444 Al 16 May 2013 (16.05.2013) W P O P C T
    (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2013/070444 Al 16 May 2013 (16.05.2013) W P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every A23G 4/00 (2006.01) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, (21) International Application Number: BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, PCT/US20 12/062043 DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (22) International Filing Date: HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, 26 October 2012 (26.10.2012) KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, (25) Filing Language: English NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, (26) Publication Language: English RW, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, (30) Priority Data: ZM, ZW. 61/556,546 7 November 20 11 (07. 11.201 1) US (84) Designated States (unless otherwise indicated, for every (71) Applicant (for all designated States except US): WVI. kind of regional protection available): ARIPO (BW, GH, WRIGLEY JR. COMPANY [US/US]; 1132 Blackhawk GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, Street, Chicago, IL 60642 (US).
    [Show full text]
  • Monosaccharides: a Tof-SIMS Reference Accession #: 01592, 01593, 01594, 01595, 01596, 01597, 01598, Spectra Database
    Monosaccharides: A ToF-SIMS reference Accession #: 01592, 01593, 01594, 01595, 01596, 01597, 01598, spectra database. II. Positive polarity 01599, 01600, 01601, 01602, a) 01603, 01604, 01605, 01606, Laetitia Bernard, Rowena Crockett, and Maciej Kawecki 01607, 01608, 01609, 01610 Laboratory of Nanoscale Materials Science, Empa, CH-8600 Dübendorf, Switzerland Technique: SIMS (Received 20 August 2019; accepted 30 October 2019; published 3 December 2019) Host Material: Silicon (100) wafer The number of time-of-flight secondary ion mass spectrometry studies on biological tissues and Instrument: IONTOF TOF-SIMS.5 cells has strongly increased since the development of primary ion sources that allow not only ele- Major Species in Spectra: C, H, O, (N) mental but also molecular analysis. Substantial fragmentation during ionic bombardment results in a Minor Species in Spectra: Na, K large number of peaks, rendering data analysis complex. Complete and trustable sets of reference spectra for the main biological building blocks, i.e., amino acids, monosaccharides, fatty acids, and Published Spectra: 19 nucleotides, are required. This work aims to provide an accurate and extensive library of reference Spectra in Electronic Record: 19 + spectra for monosaccharides, measured with the Bi3 primary ion. Here (Paper II), the positive polar- Published Figures: 20 ity spectra and lists of associated characteristic fragments are presented. Published by the AVS. Spectral Category: Reference https://doi.org/10.1116/1.5125103 Keywords: ToF-SIMS, carbohydrate, sugar, monosaccharide, mass spectrometry, fragmentation INTRODUCTION Fluka and all others from Sigma Aldrich. Each powder was dissolved in freshly de-ionized H2O (resistivity >18.2 MΩ cm) Monosaccharides are the building blocks of structural polymers at a concentration of 0.1M.
    [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]
  • United States Patent (19 11) 4,312,979 Takemoto Et Al
    United States Patent (19 11) 4,312,979 Takemoto et al. 45 Jan. 26, 1982 54 POLYSACCHARIDES CONTAINING 58) Field of Search ......................... 536/1, 18, 114, 4; ALLOSE 435/101 (75) Inventors: Hisao Takemoto; Tatsuo Igarashi, (56) References Cited both of Shin-Nanyo, Japan U.S. PATENT DOCUMENTS 73 Assignee: Toyo Soda Manufacturing Co., Ltd., 3,711,462 l/1973 Abdo et al. ............................. 536/1 Tokyo, Japan 4,186,025 l/1980 Kang et al. ............................. 536/1 Primary Examiner-Johnnie R. Brown (21) Appl. No.: 30,444 Attorney, Agent, or Firm-Scully, Scott, Murphy & Presser 22 Filed: Apr. 16, 1979 57 ABSTRACT 30 Foreign Application Priority Data A new polysaccharide including allose as a constituent Apr. 20, 1978 JP Japan .................................. 53.45918 sugar and further characterized by galactose as a major Dec. 5, 1978 JP Japan ................................ 53-149715 constituent sugar is described. The polysaccharide is produced extracellularly by cultivation of Pseudomonas 51) Int. Cl. ............................................... CO7H1/08 viscogena strains in nutrient medium. 52 U.S. C. ...... 0 a a 4 536/1; 435/72; 435/101; 536/114 6 Claims, 2 Drawing Figures U.S. Patent Jan. 26, 1982 Sheet 1 of 2 4,312,979 8 O O Sn Cd O ar - O - 3 CD won L Cd O CO ve O Cd Cd cN O O O N O O o O o O O. d o o O a. 3 c) do N. ud to at Y on 9 (%) AONWLLIWSNW U.S. Patent Jan. 26, 1982 Sheet 2 of 2 4,312,979 3 s 8 un co, t OO O) O S s S 8 & O O O O O r ONWSOS9W 4,312,979 1.
    [Show full text]
  • Biochemistry Introductory Lecture Dr
    Biochemistry Introductory lecture Dr. Munaf S. Daoud Carbohydrates (CHO) Definition: Aldehyde or Ketone derivatives of the higher polyhydric alcohols or compounds which yield these derivatives on hydrolysis. Classification: (mono, di, oligo, poly) saccharide. Monosaccharides: Can be classified as trioses, tetroses, pentoses, hexoses and heptoses depending upon the number of carbon atoms, and as aldoses or ketoses, depending upon whether they have an aldehyde or ketone group. Aldehyde (-CHO) Aldoses Ketone (-C=O) Ketoses Polysaccharides (glycans): Homopolysaccharides (homoglycans): e.g. starch, glycogen, inulin, cellulose, dextrins, dextrans. Heteropolysaccharides (heteroglycans): e.g. mucopolysaccharides (MPS) or glycosaminoglycans. Function of CHO: 1) Chief source of energy (immediate and stored energy). 2) Constituent of compound lipids and conjugated protein. 3) Structural element like cellulose. 4) Drugs like cardiac glycosides and antibodies. 5) Lactating mammary gland (Lactose in milk). 6) Synthesis of other substances like fatty acids, cholesterol, amino acids…etc. by their degradation products. 7) Constituent of mucopolysaccharides. 1 1) Stereo-isomerism Stereo-isomers: D-form, L-form 2) Optical isomers (optical activity) Enantiomers: dextrorotatory (d or + sign) Levorotatory (l or – sign) Racemic (d l) 3) Cyclic structures or open chain 4) Anomers and Anomeric carbon OH on carbon number 1, if below the plane then its -form, if above the plane then -form. Mutarotation: the changes of the initial optical rotation that takes place
    [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]
  • REPORTS Two-Step Synthesis of Carbohydrates
    R ESEARCH A RTICLES and Mgm1 have been demonstrated and in- additional evolutionary connection between 10. More information about Fzo1 is available at volve the outer membrane fusion protein Ugo1 DRPs and endosymbiotic organelles is that their http://db.yeastgenome.org/cgi-bin/SGD/homolog/ nrHomolog?locusϭYBR179C#summary. (7, 8). The exact nature of the interactions be- division also has evolved to require the action of 11. G. J. Praefcke, H. T. McMahon, Nature Rev. Mol. Cell tween Fzo1, Ugo1, and Mgm1 and their specif- a DRP (25). Biol. 5, 133 (2004). ic roles in mitochondrial fusion remain largely DRPs most commonly have been shown to 12. S. Frank et al., Dev. Cell 1, 515 (2001). unknown. However, Ugo1 functions as an function in membrane fission events, such as 13. M. Karbowski et al., J. Cell Biol. 159, 931 (2002). 14. M. Karbowski et al., J. Cell Biol. 164, 493 (2004). adaptor between Fzo1 and Mgm1 (18). Fzo1 mitochondrial and chloroplast division and en- 15. C. Alexander et al., Nature Genet. 26, 211 (2000). interactions with inner membrane components docytosis (26). However, the actions of two 16. C. Delettre et al., Nature Genet. 26, 207 (2000). may be required in a mechanical manner for the DRPs, Fzo1 on the outer membrane and Mgm1 17. S. Zuchner et al., Nature Genet. 36, 449 (2004). formation of regions of close inner and outer on the inner membrane, are required for mito- 18. H. Sesaki, R. E. Jensen, J. Biol. Chem. 279, 28298 (2004). 19. Materials and methods are available as supporting membrane contact within mitochondria.
    [Show full text]
  • Ose: an Editorial on Carbohydrate Nomenclature Neil P
    Gly l of cob na io r lo u g o y J Price et al., J Glycobiol 2012, 1:2 Journal of Glycobiology DOI: 10.4172/2168-958X.1000e105 ISSN: 2168-958X Editorial Open Access The Name of the – ose: An Editorial on Carbohydrate Nomenclature Neil P. J. Price* National Center for Agricultural Utilization Research, U.S. Department of Agriculture, Agricultural Research Service, 1815 N. University St., Peoria, IL 61604, USA What’s in a name? The term ‘sugar’ is usually applied to the configuration of theD -aldopentose sugars. Perhaps I can suggest “Ribs monosaccharides, disaccharides, and lower oligosaccharides. Are X-rayed Last” for the series ribose, arabinose, xylose, lyxose, so Historically, sugars were often named after their source, for example, that they also conform to the above rules. grape sugar for glucose, cane sugar for saccharose (later called sucrose), Let’s just take the three most commonly occurring hexose sugars, wood sugar for xylose, and fruit sugar for fructose (fruchtzucker, glucose, galactose, and mannose. The IUPAC name for D-glucose is fructose). The term ‘carbohydrate’ (from the French ‘hydrate de (2R,3S,4R,5R)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrol, carbone’) was originally used only for monosaccharides, because although this is used only rarely. By this nomenclature, D-galactose is their composition can be expressed as C (H O) . Glucose was named n 2 n called (2R,3S,4S,5R)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5- in 1838, although much later than this Kekule suggested ‘dextrose’ tetrol and D-mannose is (2S,3S,4R,5R)-6-(hydroxymethyl)tetrahydro- because glucose is dextrorotatory.
    [Show full text]
  • Chapter 4 Specificity and Affinity
    CHAPTER 4 SPECIFICITY AND AFFINITY The hallmark of lectins is the ability to bind carbohydrates specifically and reversibly. Understanding the properties and functions of lectins, as well as using them for diverse purposes, requires knowledge of this specificity, which is the major topic of the present chapter. Several lectins combine also with non-carbohydrate ligands, either at their carbohydrate binding sites or at sites distinct from the latter. A few others possess enzymatic activity unrelated to their carbohydrate specificity. These will be discussed briefly at the end of the chapter. 4.1 METHODOLOGY Studies of the carbohydrate specificity of lectins are customarily performed by the hapten inhibition technique, in which different monosaccharides, oligosaccharides, or glycopeptides, are tested for their ability to inhibit either hemagglutination (see Fig. 3.1) (Rüdiger, 1993) or polysaccharide (or glycoprotein) precipitation by the lectin (see Fig. 3.2) (Goldstein, 1976). Alternately, either the carbohydrate or the lectin is immobilized in the wells of a microtiter plate and the inhibitory effect of different saccharides on the interaction of the immobilized one with its partner in solution is assayed. Using specially designed glycochips (see 3.1) with different mono- and oligosaccharides, the specificity of a lectin can be determined (Fig. 4.1). These techniques are simple, rapid and require submilligram amounts of material. They stem from the observations of Landsteiner, made in the early part of the last century, that a simple substance with a structure closely related to, or identical with, the immunological determinant group of an antigen can combine with the antibody and thereby competitively inhibit the antigen-antibody reaction.
    [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]
  • An Introduction to Polysaccharide Biotechnology, Second Edition
    BIOCHEMISTRY BIOTECHNOLOGY AN INTRODUCTION TO POLYSACCHARIDE Stephen E. Harding • Michael P. Tombs An Introduction to Gary G. Adams • Berit Smestad Paulsen POLYSACCHARIDE Kari Tvete Inngjerdingen • Hilde Barsett BIOTECHNOLOGY An Introduction to SECOND EDITION Polysaccharides and related high molecular weight glycans are hugely diverse with wide application in biotechnology and great opportunities for further exploitation. POLYSACCHARIDE An Introduction to Polysaccharide Biotechnology – a second edition of the popular original text by Tombs and Harding – introduces students, researchers, clinicians and industrialists to the properties of some of the key materials involved, how these are applied, some of the economic factors concerning their production and how they BIOTECHNOLOGY are characterised for regulatory purposes. FEATURES • Basic properties of polysaccharides and how they are very different to proteins SECOND EDITION • How these properties are affected by enzymes and how the effects of enzymes can be controlled • An introduction to some ‘patent preferred’ methodologies for polysaccharide EDITION SECOND characterisation, such as molecular weight distribution • Applications in biopharma, food and other industries • The application of marker-assisted selection to fruit ripening and preservation, the development of glycovaccines against meningitis and other serious diseases • Barsett Paulsen • Inngjerdingen • Adams Harding • Tombs • A whole chapter dedicated to a case study on bioactivity and how modern research is unlocking the way polysaccharides are at the core of many HG HG traditional medicines • Further Reading sections for follow up K23616 6000 Broken Sound Parkway, NW Suite 300, Boca Raton, FL 33487 RG-I RG-II 711 Third Avenue New York, NY 10017 2 Park Square, Milton Park Abingdon, Oxon OX14 4RN, UK www.crcpress.com An Introduction to Polysaccharide Biotechnology An Introduction to Polysaccharide Biotechnology By Stephen E.
    [Show full text]