ArticleOrganic & biomolecular chemistry2011
Nucleotidylation of unsaturated carbasugar in validamycin biosynthesis.
Article in Organic & biomolecular chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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12 citing papers in PubMed, 28 citations in OpenAlex.
- NonglycosidicSynthetic and systems biotechnology · 2025Article
- Synthesis of the Carba-Analogs of the α-Pyranose and β-Pyranose Forms of Sedoheptulose 7-Phosphate and Probing the Stereospecificity of Sedoheptulose 7-Phosphate Cyclases.Biochemistry · 2024Article
- Catalytic Mechanism of Nonglycosidic C-N Bond Formation by the Pseudoglycosyltransferase Enzyme VldE.ACS catalysis · 2023Article
- Biochemical Characterization of GacI, a Bifunctional Glycosyltransferase-Phosphatase Enzyme Involved in Acarbose Biosynthesis inBiochemistry · 2022Article
- Complete biosynthetic pathway to the antidiabetic drug acarbose.Nature communications · 2022Article
- Synthesis of novel seven-membered carbasugars and evaluation of their glycosidase inhibition potentials.RSC advances · 2021Article
- Glycosylation of acyl carrier protein-bound polyketides during pactamycin biosynthesis.Nature chemical biology · 2019Article
- Biosynthesis and Metabolic Engineering of Pseudo-oligosaccharides.Emerging topics in life sciences · 2018Article
- Distinct Substrate Specificity and Catalytic Activity of the Pseudoglycosyltransferase VldE.Chemistry & biology · 2015Article
- Genomic and transcriptomic insights into the thermo-regulated biosynthesis of validamycin in Streptomyces hygroscopicus 5008.BMC genomics · 2012Article
- Biosynthetic origin and mechanism of formation of the aminoribosyl moiety of peptidyl nucleoside antibiotics.Journal of the American Chemical Society · 2011Article
- Pseudoglycosyltransferase catalyzes nonglycosidic C-N coupling in validamycin a biosynthesis.Journal of the American Chemical Society · 2011Article
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Authors and funding
6 authors at 2 institutions in 2 countries.
Funding
Abstract
Validamycin A is a member of microbial-derived C(7)N-aminocyclitol family of natural products that is widely used as crop protectant and the precursor of the antidiabetic drug voglibose. Its biosynthetic gene clusters have been identified in several Streptomyces hygroscopicus strains, and a number of genes within the clusters have been functionally analyzed. Of these genes, valB, which encodes a sugar nucleotidyltransferase, was found through inactivation study to be essential for validamycin biosynthesis, but its role was unclear. To characterize the role of ValB in validamycin biosynthesis, four carbasugar phosphate analogues were synthesized and tested as substrate for ValB. The results showed that ValB efficiently catalyzes the conversion of valienol 1-phosphate to its nucleotidyl diphosphate derivatives, whereas other unsaturated carbasugar phosphates were found to be not the preferred substrate. ValB requires Mg(2+), Mn(2+), or Co(2+) for its optimal activity and uses the purine-based nucleotidyltriphosphates (ATP and GTP) more efficiently than the pyrimidine-based NTPs (CTP, dTTP, and UTP) as nucleotidyl donor. ValB represents the first member of unsaturated carbasugar nucleotidyltransferases involved in natural products biosynthesis. Its characterization not only expands our understanding of aminocyclitol-derived natural products biosynthesis, but may also facilitate the development of new tools for chemoenzymatic synthesis of carbohydrate mimetics.
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