ArticleOrganic letters2007
Synthesis and analysis of substrate analogues for UDP-galactopyranose mutase: implication for an oxocarbenium ion intermediate in the catalytic mechanism.
Article in Organic letters, 2007. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 51 citations in OpenAlex.
- N5 Is the New C4a: Biochemical Functionalization of Reduced Flavins at the N5 Position.Frontiers in molecular biosciences · 2020Review
- Recent Advances in the Synthesis of Glycoconjugates for Vaccine Development.Molecules (Basel, Switzerland) · 2018Review
- Conformational Control of UDP-Galactopyranose Mutase Inhibition.Biochemistry · 2017Article
- Study of Uridine 5'-Diphosphate (UDP)-Galactopyranose Mutase Using UDP-5-Fluorogalactopyranose as a Probe: Incubation Results and Mechanistic Implications.Organic letters · 2016Article
- Virtual Screening for UDP-Galactopyranose Mutase Ligands Identifies a New Class of Antimycobacterial Agents.ACS chemical biology · 2015Article
- Sigma S-dependent antioxidant defense protects stationary-phase Escherichia coli against the bactericidal antibiotic gentamicin.Antimicrobial agents and chemotherapy · 2014Article
- Structure, mechanism, and dynamics of UDP-galactopyranose mutase.Archives of biochemistry and biophysics · 2014Review
- The structural biology of enzymes involved in natural product glycosylation.Natural product reports · 2012Review
- Nucleophilic participation of reduced flavin coenzyme in mechanism of UDP-galactopyranose mutase.The Journal of biological chemistry · 2012Article
- Synthetic UDP-furanoses as potent inhibitors of mycobacterial galactan biogenesis.Chemistry & biology · 2010Article
- Characterization of a bifunctional pyranose-furanose mutase from Campylobacter jejuni 11168.The Journal of biological chemistry · 2010Article
- Ligand binding and substrate discrimination by UDP-galactopyranose mutase.Journal of molecular biology · 2009Article
- Sugar nucleotide recognition by Klebsiella pneumoniae UDP-D-galactopyranose mutase: fluorinated substrates, kinetics and equilibria.Organic & biomolecular chemistry · 2009Article
- Potent ligands for prokaryotic UDP-galactopyranose mutase that exploit an enzyme subsite.Organic letters · 2009Article
- The diverse roles of flavin coenzymes--nature's most versatile thespians.The Journal of organic chemistry · 2007Review
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
[reaction: see text] UDP-D-galactofuranose (2), which is essential for both cell growth and virulence in many pathogenic microorganisms, is converted from UDP-D-galactopyranose (UDP-Galp, 1) by the flavin adenine dinucleotide (FAD)-dependent enzyme UDP-galactopyranose mutase (UGM). Here, we report the synthesis of UDP-GalOH (13) and show it as an inhibitor for UGM with a binding affinity similar to that of 1. These results are more consistent with a mechanism involving an oxocarbenium ion intermediate in UGM catalysis.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.