title: Study of Uridine 5'-Diphosphate (UDP)-Galactopyranose Mutase Using UDP-5-Fluorogalactopyranose as a Probe: Incubation Results and Mechanistic Implications.
abstract: Uridine 5'-diphosphate-5-fluorogalactopyranose (UDP-5F-Galp, 7) was synthesized, and its effect on UDP-Galp mutase (UGM) was investigated. UGM facilitated the hydrolysis of 7 to yield UDP and 5-oxogalactose (24), but no 11 was detected. (19)F NMR and trapping experiments demonstrated that the reaction involves the initial formation of a substrate-cofactor adduct followed by decomposition of the resulting C5 gem-fluorohydrin to generate a 5-oxo intermediate (10). The results support the current mechanistic proposal for UGM and suggest new directions for designing mechanism-based inhibitors.
authors.affiliation: Department of Chemistry, The University of Texas at Austin , Austin, Texas 78712, United States.
authors.forename: Geng-Min
authors.initials: GM
authors.lastname: Lin
authors.affiliation: Division of Chemical Biology and Medicinal Chemistry, College of Pharmacy, The University of Texas at Austin , Austin, Texas 78712, United States.
authors.forename: He G
authors.initials: HG
authors.lastname: Sun
authors.affiliation: Department of Chemistry, The University of Texas at Austin , Austin, Texas 78712, United States.|Division of Chemical Biology and Medicinal Chemistry, College of Pharmacy, The University of Texas at Austin , Austin, Texas 78712, United States.
authors.forename: Hung-Wen
authors.initials: HW
authors.lastname: Liu
mesh_terms: D057075:Enzyme Assays; D005182:Flavin-Adenine Dinucleotide / Q000737:chemistry; D005690:Galactose / Q000031:analogs & derivatives* / Q000737:chemistry*; D019751:Intramolecular Transferases / Q000737:chemistry*; D014530:Uridine Diphosphate / Q000031:analogs & derivatives* / Q000737:chemistry*
chemical_list: D005182:Flavin-Adenine Dinucleotide; D014530:Uridine Diphosphate; D019751:Intramolecular Transferases; C098051:UDP-galactopyranose mutase; D005690:Galactose