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Glucose Moieties (glucose + moiety)
Selected AbstractsMetabolic engineering of Saccharomyces cerevisiae for the synthesis of the wine-related antioxidant resveratrolFEMS YEAST RESEARCH, Issue 1 2003John V.W. Becker Abstract The stilbene resveratrol is a stress metabolite produced by Vitis vinifera grapevines during fungal infection, wounding or UV radiation. Resveratrol is synthesised particularly in the skins of grape berries and only trace amounts are present in the fruit flesh. Red wine contains a much higher resveratrol concentration than white wine, due to skin contact during fermentation. Apart from its antifungal characteristics, resveratrol has also been shown to have cancer chemopreventive activity and to reduce the risk of coronary heart disease. It acts as an antioxidant and anti-mutagen and has the ability to induce specific enzymes that metabolise carcinogenic substances. The objective of this pilot study was to investigate the feasibility of developing wine yeasts with the ability to produce resveratrol during fermentation in both red and white wines, thereby increasing the wholesomeness of the product. To achieve this goal, the phenylpropanoid pathway in Saccharomyces cerevisiae would have to be introduced to produce p -coumaroyl-CoA, one of the substrates required for resveratrol synthesis. The other substrate for resveratrol synthase, malonyl-CoA, is already found in yeast and is involved in de novo fatty-acid biosynthesis. We hypothesised that production of p -coumaroyl-CoA and resveratrol can be achieved by co-expressing the coenzyme-A ligase-encoding gene (4CL216) from a hybrid poplar and the grapevine resveratrol synthase gene (vst1) in laboratory strains of S. cerevisiae. This yeast has the ability to metabolise p -coumaric acid, a substance already present in grape must. This compound was therefore added to the synthetic media used for the growth of laboratory cultures. Transformants expressing both the 4CL216 and vst1 genes were obtained and tested for production of resveratrol. Following ,-glucosidase treatment of organic extracts for removal of glucose moieties that are typically bound to resveratrol, the results showed that the yeast transformants had produced the resveratrol ,-glucoside, piceid. This is the first report of the reconstruction of a biochemical pathway in a heterologous host to produce resveratrol. [source] Well-defined glycopolymer amphiphiles for liquid and supercritical carbon dioxide applicationsJOURNAL OF POLYMER SCIENCE (IN TWO SECTIONS), Issue 21 2001Weijun Ye Abstract Well-defined D -glucose-containing glycopolymers, poly(3- O -methacryloyl-1,2 : 5,6-di- O -isopropylidene- D -glucofuranose) (PMAIpGlc), and diblock copolymers of PMAIpGlc with poly(1,1-dihydroperfluorooctyl methacrylate) (PFOMA) were synthesized by living anionic polymerization in THF at ,78 °C with 1,1-diphenylhexyllithium in the presence of lithium chloride. The resulting polymers were found to possess predictable molecular weights and very narrow molecular weight distributions (MWD, Mw/Mn , 1.16). Removal of the acetal protective groups from the protected glycopolymer block copolymer was carried out using 90% trifluoroacetic acid at room temperature, yielding a hydrophilic block copolymer with pendant glucose moieties. Both protected (lipophilic/CO2 -philic) and deprotected (hydrophilic/CO2 -philic) fluorocopolymers were proved to be CO2 amphiphiles. Their solubility in CO2 was heavily influenced by the amphiphilic structure, such as the copolymer compositions and the polarities of sugar block. Light-scattering studies showed that, after removal of the protective groups, the deprotected block copolymer formed aggregate structures in liquid CO2 with an average micellar size of 27 nm. © 2001 John Wiley & Sons, Inc. J Polym Sci Part A: Polym Chem 39: 3841,3849, 2001 [source] Variation in oxygen isotope fractionation during cellulose synthesis: intramolecular and biosynthetic effectsPLANT CELL & ENVIRONMENT, Issue 10 2006LEONEL STERNBERG ABSTRACT The oxygen isotopic composition of plant cellulose is commonly used for the interpretations of climate, ecophysiology and dendrochronology in both modern and palaeoenvironments. Further applications of this analytical tool depends on our in-depth knowledge of the isotopic fractionations associated with the biochemical pathways leading to cellulose. Here, we test two important assumptions regarding isotopic effects resulting from the location of oxygen in the carbohydrate moiety and the biosynthetic pathway towards cellulose synthesis. We show that the oxygen isotopic fractionation of the oxygen attached to carbon 2 of the glucose moieties differs from the average fractionation of the oxygens attached to carbons 3,6 from cellulose by at least 9%, for cellulose synthesized within seedlings of two different species (Triticum aestivum L. and Ricinus communis L.). The fractionation for a given oxygen in cellulose synthesized by the Triticum seedlings, which have starch as their primary carbon source, is different than the corresponding fractionation in Ricinus seedlings, within which lipids are the primary carbon source. This observation shows that the biosynthetic pathway towards cellulose affects oxygen isotope partitioning, a fact heretofore undemonstrated. Our findings may explain the species-dependent variability in the overall oxygen isotope fractionation during cellulose synthesis, and may provide much-needed insight for palaeoclimate reconstruction using fossil cellulose. [source] Polymerase-Catalysed Incorporation of Glucose Nucleotides into a DNA DuplexCHEMISTRY - A EUROPEAN JOURNAL, Issue 22 2009Marleen Renders Abstract Active but unselective: Nucleoside triphosphates possessing glucose moieties (such as those depicted) instead of the natural furanose rings are recognised by the active sites of polymerases. Polymerases therefore seem to be very unspecific in their recognition patterns. The enzymatic recognition of six-membered ring nucleoside triphosphates,in particular the 6,-triphosphates of (,- D -glucopyranosyl)thymine, (2,,3,-dideoxy-,- D -glucopyranosyl)thymine, (3,,4,-dideoxy-,- D -glucopyranosyl)thymine and (2,,3,-dideoxy-,- D -glucopyranosyl)adenine,was investigated. Despite the facts that the pyranose nucleic acids obtained by polymerisation of these monomers do not hybridise in solution with DNA and that the geometry of a DNA strand in a natural duplex differs from that of a pyranose nucleic acid, elongation of the DNA duplex with all four nucleotide analogues by Vent,(exo,) polymerase was observed. Modelling experiments showed that hydrogen bonds are formed when 2,,3,-dideoxy-,-homo-T building blocks or ,- D - gluco -T building blocks are incorporated opposite adenosine residues in the template but not when they are incorporated opposite thymine residues in the template. The model shows a near perfect alignment of a secondary hydroxy group at the end of the primer and the ,-phosphate group of the incoming triphosphate. The results of these experiments provide new information on the role of the active site of the enzyme in the polymerisation reaction. [source] Liquid chromatography coupled to nuclear magnetic resonance spectroscopy for the identification of isoflavone glucoside malonates in T. pratense L. leaves.JOURNAL OF SEPARATION SCIENCE, JSS, Issue 13 2004Eva de Rijke Abstract Previous studies revealed that the main isoflavones in extracts of leaves of T. pratense L. are biochanin A and formononetin, their 7- O -glucosides, and two glucoside malonate isomers of each of them. Since LC,MS(/MS) did not provide sufficient information to distinguish the glucoside malonate isomers, in the present paper LC,NMR as well as off-line two-dimensional NMR were used to obtain further structural information. Matrix solid-phase dispersion (MSPD) was applied to obtain sufficiently high analyte concentrations to perform LC,NMR. Stop-flow reversed-phase LC,NMR was performed using a gradient of deuterated water and deuterated acetonitrile. Off-line COSY and NOESY experiments were carried out to determine the positions of the glucose moiety on the flavonoid aglycone, and of the malonate moiety on the glucose. Based on the fragmentation patterns in MS/MS and the NMR spectra, the two formononetin glucoside malonate isomers were identified as 7- O -,-D-glucoside 6´´- O -malonate and 7- O -,-D-glucoside 4´´- O -malonate; i.e. they only differ in the substitution position of the malonate group on the glucoside ring. The biochanin A glucoside malonate isomers, however, have quite different structures. The main and later eluting isomer is biochanin A 7- O -,-D-glucoside 6´´- O -malonate, and the minor and earlier eluting isomer is 5-hydroxy-7-methoxyisoflavone 4´- O -,-D-glucoside 4´´- O -malonate: the positions of the methoxy group and the glucoside 6´´- O -malonate group on the flavonoid skeleton are interchanged. [source] Enhanced post-source decay and cross-ring fragmentation of oligosaccharides facilitated by conversion to amino derivativesRAPID COMMUNICATIONS IN MASS SPECTROMETRY, Issue 13 2004Jan Muzikar Post-source decay (PSD) fragmentation of chemically or enzymatically produced aminoglycans has been evaluated through matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry. Conversion of native glycans to their respective aminoglycan derivatives improved detection sensitivity of the usual fragments and promoted cross-ring fragmentation of linear oligosaccharides, facilitating linkage recognition. The cross-ring fragmentations for both dextrin and dextran oligosaccharides were not limited to the reducing-end glucose moiety, as they were extended throughout the entire molecule. When the amino group was generated for N-glycans derived from three different glycoproteins, an enhancement of PSD was observed, without a significant extent of cross-ring fragmentation. Copyright © 2004 John Wiley & Sons, Ltd. [source] | |||||||||||||