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Nucleoside Diphosphate Sugars (4):
Recent article
Nucleoside Diphosphate Sugars
Abstract
We successfully isolated approximately 24 mg/L 3-O-rhamnosyl quercetin and 12.9 mg/L 3-O-rhamnosyl kaempferol upon feeding of 0.2 mM of the respective flavonoids and were also able to isolate 3-O-allosyl quercetin. Thus, this study reveals a method that might be useful for the biosynthesis of rhamno...
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PMID: 20506539
PDF is available here.
PDF is available here.
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Journal of Bacteriology (190)21 2008
Abstract
We explored the acceptor substrate promiscuity and polymer length disregulation that appear to be characteristic of TagF activity away from biological membranes. Using isotope labeling, steady-state kinetics, and chemical lability studies, we demonstrated that the enzyme can synthesize poly(glycerol...
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PMID: 18723614
PDF is available here.
PDF is available here.
Biochemical Journal (413)1 2008
Abstract
ADPRibase-Mn (Mn2+-dependent ADP-ribose/CDP-alcohol pyrophosphatase) was earlier isolated from rat liver supernatants after separation from ADPRibase-I and ADPRibase-II (Mg2+-activated ADP-ribose pyrophosphatases devoid of CDP-alcohol pyrophosphatase activity). The last mentioned are putative Nudix...
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PMID: 18352857
PDF is available here.
PDF is available here.
Abstract
Forosamine (4-dimethylamino)-2,3,4,6-tetradeoxy-beta-D-threo-hexopyranose) is a highly deoxygenated sugar component of several important natural products, including the potent yet environmentally benign insecticide spinosyns. To study D-forosamine biosynthesis, the five genes (spnO, N, Q, R, and S)...
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PMID: 18345667
PDF is available here.
PDF is available here.
Carbohydrate Research (343)2 2008
Abstract
We investigated the specificity of glycosyltransferases toward donor substrates in two complementary directions. First we prepared simple N-acetyl-alpha-D-glucosamine 1-diphosphates: methyl-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-diphosphate, benzyl-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-...
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PMID: 18048019
PDF is available here.
PDF is available here.
Abstract
Six different glycosyl esters of nucleoside pyrophosphates (monosaccharide nucleotides) were analyzed by means of matrix-assisted laser desorption/ionisation reflectron time-of-flight mass spectrometry (MALDI/RToF MS) in the negative ion mode. Several matrices were evaluated and 3-hydroxypicolinic a...
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PMID: 19136728
PDF is available here.
PDF is available here.
ChemBioChem (8)17 2007
Abstract
Substrate flexibility of vicenisaminyltransferase VinC involved in the biosynthesis of vicenistatin.
Abstract
These results indicate that VinC is a unique glycosyltransferase possessing broad substrate specificity. The mechanism of this axially oriented glycosidic bond formation from the equatorially oriented dTDP-sugar might be explained by conformational change of dTDP-sugar to a boat conformation during...
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PMID: 17388594
PDF is available here.
PDF is available here.
Organic Letters (9)7 2007
Abstract
We report a novel stereoselective route to UDP- and GDP-alpha-D-mannose as well as UDP- and GDP-beta-L-fucose via direct displacement of acylated glycosyl bromides with nucleoside 5'-diphosphates....
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PMID: 17338534
PDF is available here.
PDF is available here.
FEBS Letters (581)5 2007
Abstract
Escherichia coli ADP-sugar pyrophosphatase (AspP) is a "Nudix" hydrolase that catalyzes the hydrolytic breakdown of ADP-glucose linked to glycogen biosynthesis. Moderate increases of AspP activity in the cell are accompanied by significant reductions of the glycogen content. In vitro analyses showed...
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PMID: 17306798
PDF is available here.
PDF is available here.
Carbohydrate Research (342)3-4 2007
Abstract
The direct oxidation of UDP-alpha-d-glucose and UDP-N-acetyl-alpha-d-glucosamine to the corresponding uronic acids was explored using either TEMPO or platinum-catalysed oxidation with molecular oxygen. Whilst TEMPO-based procedures gave rise to substantial over-oxidation and/or degradation of UDP-gl...
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PMID: 17087923
PDF is available here.
PDF is available here.
Glycobiology (17)2 2007
Abstract
We have cloned and heterologously overexpressed gerK1 in Escherichia coli BL21 (DE3) cells. This gene encodes for a protein with the putative function of a dTDP-4-keto-6-deoxyglucose reductase, which appears to be involved in the dihydrochalcomycin (GERI-155) biosynthesis evidenced by Streptomyces s...
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PMID: 17053005
PDF is available here.
PDF is available here.
Journal of Molecular Biology (365)1 2007
Abstract
We report the structure of RmlC from several organisms in complex with product and product mimics. We have probed site-directed mutants by assay and by deuterium exchange. The combination of structural and biochemical data has allowed us to assign key residues and identify the conformation of the ca...
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PMID: 17046787
PDF is available here.
PDF is available here.
Abstract
Approximately 80% of secreted and membrane proteins (40% of all proteins) of eukaryotes become covalently linked to sugars in the lumen of the Golgi apparatus, a cellular organelle that is part of the secretory system of all eukaryotes. The sugar donors are mostly nucleoside diphosphate sugars (nucl...
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PMID: 17115720
PDF is available here.
PDF is available here.
Abstract
We report the production of one family of rhamnolipids, specifically the monorhamnolipids, and of HAAs in a recombinant Escherichia coli strain expressing P. aeruginosa rhlAB operon. We found that the availability in E. coli of dTDP-L: -rhamnose, a substrate of RhlB, restricts the production of mono...
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PMID: 16847602
PDF is available here.
PDF is available here.
Biochemistry (Washington) (45)40 2006
Abstract
A biosynthetic pathway is proposed for creating 6-deoxy-5-ketofructose-1-phosphate (DKFP), a precursor sugar for aromatic amino acid biosynthesis in Methanocaldococcus jannaschii. First, two possible routes were investigated to determine if a modified, established biosynthetic pathwa...
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PMID: 17014089
PDF is available here.
PDF is available here.
Abstract
We report that four glycosyltransferases from two distinct natural product biosynthetic pathways-calicheamicin and vancomycin-readily catalyze reversible reactions, allowing sugars and aglycons to be exchanged with ease. As proof of the broader applicability of these new reactions, more than 70 diff...
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PMID: 16946071
PDF is available here.
PDF is available here.
Abstract
These results suggest that, even though there appear to be a fair number of genes encoding for NSTs, they are not functionally redundant and seem to play specific roles in glycosylation....
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PMID: 16981043
PDF is available here.
PDF is available here.
Abstract
Abstract
This report describes a procedure combining six enzymes native to Escherichia coli or Salmonella typhi, such as thymidine kinase (TK), thymidylate kinase (TMK), nucleoside diphosphate kinase (NDK), pyruvate kinase (PK; for ATP regeneration), TDP-glucose synthetase (RfbA), and TDP-glucose 4,6-dehydra...
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PMID: 16448097
PDF is available here.
PDF is available here.
Analytical Biochemistry (348)2 2006
Abstract
Analysis of intracellular nucleotide and nucleotide sugar contents is essential in studying protein glycosylation of mammalian cells. Nucleotides and nucleotide sugars are the donor substrates of glycosyltransferases, and nucleotides are involved in cellular energy metabolism and its regulation. A s...
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PMID: 16325757
PDF is available here.
PDF is available here.
Abstract
dTDP-L-rhamnose, an important precursor of O-antigen, was prepared on a large scale from dTMP by executing an one-pot reaction in which six enzymes are involved. Two enzymes, dTDP-4-keto-6-deoxy-D-glucose 3,5-epimerase and dTDP-4-keto-rhamnose reductase, responsible for the conversion of dTDP-4-keto...
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PMID: 16276532
PDF is available here.
PDF is available here.
Journal of Biological Chemistry (280)49 2005
Abstract
We show that UDP-Glc: glycoprotein glucosyltransferase-mediated glucosylation is not dependent on the presence of NDPases or on ER-Golgi vesicular traffic and that GDP-Man-dependent N- and O-mannosylations are reduced but not abolished in the absence of NDPases in the secretory pathway. Further, the...
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PMID: 16172132
PDF is available here.
PDF is available here.
ChemBioChem (6)11 2005
Abstract
Abstract
These results strongly support the role of Tyl1a as a TDP-4-keto-6-deoxy-d-glucose 3,4-isomerase....
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PMID: 16131199
PDF is available here.
PDF is available here.
ChemBioChem (6)8 2005
Abstract
A flexible enzyme module system is presented that allows preparative access to important dTDP-activated deoxyhexoses from dTMP and sucrose. The strategic combination of the recombinant enzymes dTMP-kinase and sucrose synthase (SuSy), and the enzymes RmlB (4,6-dehydratase), RmlC (3,5-epimerase) and R...
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PMID: 15977277
PDF is available here.
PDF is available here.
Microbiology (151)Pt 6 2005
Abstract
The exopolysaccharide (EPS) biosynthesis gene clusters of four Lactobacillus rhamnosus strains consist of chromosomal DNA regions of 18.5 kb encoding 17 ORFs that are highly similar among the strains. However, under identical conditions, EPS production varies considerably among these strains, from 6...
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PMID: 15941992
PDF is available here.
PDF is available here.
Chemistry & Biology (12)5 2005
Abstract
We report here that purified AknS has very low activity in the absence of the adjacently encoded AknT; however, at a 3:1 ratio, AknT stimulates AknS k(cat) by 40-fold up to 0.22 min(-1) for transfer of L-2-deoxyfucose (2-dF) to the aglycone aklavinone. It is likely that several other Gtfs that glyco...
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PMID: 15911373
PDF is available here.
PDF is available here.
Acta Crystallographica Section D (61)Pt 4 2005
Abstract
Tyvelose is a unique 3,6-dideoxyhexose found in the O antigens of some pathogenic species of Yersinia and Salmonella. It is produced via a complex biochemical pathway that employs CDP-D-glucose as the starting ligand. CDP-D-glucose 4,6-dehydratase catalyzes the first irreversible step in the synthes...
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PMID: 15805590
PDF is available here.
PDF is available here.
Abstract
We have expressed three genes to elucidate the functions of NovW, NovU, and NovS in Escherichia coli. NovW and NovU catalyze the formation of dTDP-4-keto-6-deoxy-5-C-methyl-L-lyxo-hexose from dTDP-4-keto-6-deoxy-D-glucose. NovS reduces the product formed from the reaction of NovW with dTDP-4-keto-6-...
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PMID: 15752721
PDF is available here.
PDF is available here.
Journal of Biological Chemistry (280)12 2005
Abstract
Our investigation of this protein indicates that its probable biological role is that of a nucleoside diphospho-keto-sugar aminotransferase, although the preferred keto-sugar substrate remains unknown. These experiments demonstrate the utility of a generic affinity-based ligand binding technology in...
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PMID: 15634672
PDF is available here.
PDF is available here.
ChemBioChem (6)2 2005
Abstract
A novel high-throughput screening (HTS) method with electrospray time-of-flight (ESI-TOF) mass spectrometry allows i) rapid and broad screening of multisubstrate enzyme catalytic activity towards a range of donor and acceptor substrates; ii) determination of full multisubstrate kinetic parameters an...
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PMID: 15678424
PDF is available here.
PDF is available here.
Carbohydrate Research (339)16 2004
Abstract
New unnatural sugar nucleotides, UDP-Fuc and CDP-Fuc were synthesized from fucose-beta-1-phosphate and nucleotide monophosphates activated as morpholidates. Furthermore, a nucleotide analogue was prepared by phosphorylation of 1-(beta-D-ribofuranosyl)cyanuric acid, itself obtained as a protected der...
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PMID: 15519322
PDF is available here.
PDF is available here.
Journal of Biological Chemistry (279)42 2004
Abstract
We describe the three-dimensional structure of the alpha-D-glucose-1-phosphate cytidylyltransferase from Salmonella typhi, which catalyzes the first step in the production of CDP-tyvelose. For this investigation, the enzyme was crystallized in the presence of its product, CDP-glucose. In contrast to...
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PMID: 15292268
PDF is available here.
PDF is available here.
Biochemistry (Washington) (43)37 2004
Abstract
We showed previously that CDP-ribitol synthase activity in H. influenzae is catalyzed by the bifunctional enzyme Bcs1 in a two-step reaction with reduction preceding cytidylyl transfer [Zolli, M., et al. (2001) Biochemistry 40, 5041-5048]. In the work reported here, we predicted a CDP-ribitol synthe...
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PMID: 15362865
PDF is available here.
PDF is available here.
Abstract
I hypothesise that the control of nucleotide sugar interconversion enzymes regulates glycosylation patterns in response to developmental, metabolic and stress-related stimuli, thereby linking signalling with primary metabolism and the dynamics of the extracellular matrix....
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PMID: 15134748
PDF is available here.
PDF is available here.
Analytical Biochemistry (328)2 2004
Abstract
An electrospray ionization mass spectrometry-based assay has been developed to study the class of enzymes called sugar nucleotidyltransferases that couple sugar-1-phosphates and nucleotide triphosphates to form Leloir pathway glycosyl donors. The recombinant Escherichia coli and the commercially ava...
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PMID: 15113697
PDF is available here.
PDF is available here.
Biochemistry (Washington) (43)18 2004
Abstract
We have determined the X-ray crystal structure of GtfD as a complex with TDP and the natural glycopeptide substrate at 2.0 A resolution. GtfD, a member of the bidomain GT-B glycosyltransferase superfamily, binds TDP in the interdomain cleft, while the aglycone acceptor binds in a deep crevice in the...
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PMID: 15122882
PDF is available here.
PDF is available here.
FEMS Microbiology Letters (234)1 2004
Abstract
Shigella strains are human pathogens and their identification is usually based on their O-antigens. The O-antigen gene cluster of Shigella boydii O11 was sequenced. All the expected genes for the synthesis of the O-antigen were identified on the basis of homology and genes for the biosynthesis of dT...
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PMID: 15109730
PDF is available here.
PDF is available here.
Microbiology (150)Pt 4 2004
Abstract
The approximately 16.5 kb surface layer (S-layer) glycan biosynthesis (slg) gene cluster of the Gram-positive thermophile Geobacillus stearothermophilus NRS 2004/3a has been sequenced. The cluster is located immediately downstream of the S-layer structural gene sgsE and consists of 13 ORFs that have...
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PMID: 15073305
PDF is available here.
PDF is available here.
Journal of Bacteriology (186)5 2004
Abstract
We cloned the rfbACBD operon from L. lactis MG1363, which comprises four genes involved in dTDP-rhamnose biosynthesis. When expressed in Escherichia coli, the lactococcal rfbACBD genes could sustain heterologous production of the Shigella flexneri O antigen, providing evidence of their functionality...
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PMID: 14973085
PDF is available here.
PDF is available here.
FEMS Microbiology Letters (231)2 2004
Abstract
We isolated a Tn5 mutant of A. brasilense Cd (EJ1) with an apparently modified LPS core structure, non-mucoid colony morphology, increased EPS production, and affected in maize root colonization. A 3790-bp region revealed the presence of three complete open reading frames designated rmlC, rmlB and r...
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PMID: 14987774
PDF is available here.
PDF is available here.
Abstract
A novel method employing CE-ESMS and precursor ion scanning was developed for the selective detection of nucleotide-activated sugars. By using precursor ion scanning for fragment ions specific to the different nucleotide carriers, i.e., ions at m/z 322 for cytidine monophosphate, m/z 323, 385, and 4...
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PMID: 14750855
PDF is available here.
PDF is available here.
Journal of Biological Chemistry (278)51 2003
Abstract
We describe a complex of GCT with the product, CDP-glycerol, in a crystal structure in which bound sulfate serves as a partial mimic of the second product, pyrophosphate. Binding of sulfate to form a pseudo-ternary complex is observed in three of the four chains constituting the asymmetric unit and...
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PMID: 14506262
PDF is available here.
PDF is available here.
Microbiology (149)Pt 9 2003
Abstract
The genetic variation in the dTDP-L-rhamnose pathway genes (rmlA, rmlB, rmlC and rmlD) in Vibrio cholerae was investigated. The genes are part of the O antigen gene cluster and the aim was to study lateral gene transfer of O antigen gene clusters. The rml genes of an O6 strain were cloned using an E...
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PMID: 12949172
PDF is available here.
PDF is available here.
Abstract
The hallmarks of pyridine nucleotide-dependent dehydrogenase reactions are the stereo- and regiospecific hydride transfer between the nicotinamide coenzyme and the corresponding substrate. When the hydride is delivered from NAD(P)H to reduce the keto-substrate, the site of attack is always at the ca...
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PMID: 12785757
PDF is available here.
PDF is available here.
Biochemical Society Transactions (31)Pt 3 2003
Abstract
Bacteria have a rich collection of biochemical pathways for the synthesis of complex metabolites. These conversions often involve chemical reactions that are hard to reproduce in the laboratory. An area of considerable interest is in the manipulation and synthesis of carbohydrates. In contrast with...
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PMID: 12773151
PDF is available here.
PDF is available here.
Biochemistry (Washington) (42)16 2003
Abstract
The enzyme GMD from Pseudomonas aeruginosa catalyzes the committed step in the synthesis of the exopolysaccharide alginate. Alginate is a major component of P. aeruginosa biofilms that protect the bacteria from the host immune response and antibiotic therapy. The 1.55 A crystal structure of GMD in t...
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PMID: 12705829
PDF is available here.
PDF is available here.
Biochimica et Biophysica Acta (1646)1-2 2003
Abstract
We have elucidated a steady state kinetic mechanism that is markedly different from that determined for B. subtilis TagD. Steady state kinetic experiments with recombinant, purified TarD employed a high-performance liquid chromatography assay developed in this work. The data were consistent with a t...
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PMID: 12637027
PDF is available here.
PDF is available here.
Abstract
We describe the effects of modulating the activities of glucokinase, phosphofructokinase, and phosphoglucomutase on the branching point between sugar degradation and the biosynthesis of sugar nucleotides involved in the production of exopolysaccharide biosynthesis by Lactococcus lactis. This was rea...
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PMID: 12571039
PDF is available here.
PDF is available here.
Journal of Bacteriology (185)4 2003
Abstract
CDP-2,3-di-O-geranylgeranyl-sn-glycerol:L-serine O-archaetidyltransferase (archaetidylserine synthase) activity in cell extracts of Methanothermobacter thermautotrophicus cells was characterized. The enzyme catalyzed the formation of unsaturated archaetidylserine from CDP-unsaturated archaeol and L-...
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PMID: 12562787
PDF is available here.
PDF is available here.
Molecular Microbiology (25)01 2003
Abstract
We provide data on the molecular mechanism that leads to the formation of binary encapsulated pneumococcal cells, i.e. strains that simultaneously produce type 1 and type 3 capsules. Downstream of cap1K, one truncated and three complete open reading frames homologous to those involved in the biosynt...
PDF is available here.
PDF is available here.
Abstract
We investigated the enzymes involved in the biosynthesis of thymidine diphospho-L-rhamnose (dTDP-L-rhamnose) and their specific properties. Comparable to lipopolysaccharide O-antigen biosynthesis in gram-negative bacteria, dTDP-L-rhamnose is synthesized in a four-step reaction sequence from dTTP and...
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PMID: 12147463
PDF is available here.
PDF is available here.
Acta Crystallographica Section D (58)Pt 7 2002
Abstract
The vancomycin class of antibiotics is regarded as the last line of defence against Gram-positive bacteria. The compounds used clinically are very complex organic molecules and are made by fermentation. The biosynthesis of these is complex and fascinating. Its study holds out the prospect of utilizi...
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PMID: 12077451
PDF is available here.
PDF is available here.
Journal of Bacteriology (184)12 2002
Abstract
It was determined that the dTDP-rhamnose synthesis gene, rmlD, could be inactivated in Mycobacterium smegmatis only in the presence of a rescue plasmid carrying functional rmlD. Hence, dTDP-rhamnose biosynthesis is essential for the growth of mycobacteria and the targeting of dTDP-rhamnose synthesis...
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PMID: 12029057
PDF is available here.
PDF is available here.
Infection and Immunity (69)11 2001
Abstract
We sequenced O-antigen gene clusters from Shigella boydii serotypes 4, 5, 6, and 9 and also studied the O53- and O79-antigen gene clusters of E. coli, encoding O antigens identical to those of S. boydii serotype 4 and S. boydii serotype 5, respectively. In both cases the S. boydii and E. coli O-anti...
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PMID: 11598067
PDF is available here.
PDF is available here.
Plant Molecular Biology (47)1-2 2001
Abstract
Nucleotide sugar interconversion pathways represent a series of enzymatic reactions by which plants synthesize activated monosaccharides for the incorporation into cell wall material. Although biochemical aspects of these metabolic pathways are reasonably well understood, the identification and char...
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PMID: 11554483
PDF is available here.
PDF is available here.
Abstract
Journal of Biological Chemistry (276)24 2001
Abstract
We illuminate the contributions of phosphodiester connectivity to DNA transesterification. We find that the DNA cleavage reaction was slowed by more than six orders of magnitude when a 2'-5' linkage was present at the scissile phosphodiester (CCCTT(2')p downward arrow(5')A). Thus, vaccinia topoisome...
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PMID: 11399773
PDF is available here.
PDF is available here.
Abstract
An L-rhamnosyl residue plays an essential structural role in the cell wall of Mycobacterium tuberculosis. Therefore, the four enzymes (RmlA to RmlD) that form dTDP-rhamnose from dTTP and glucose-1-phosphate are important targets for the development of new tuberculosis therapeutics. M. tuberculosis g...
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PMID: 11302803
PDF is available here.
PDF is available here.