title: Thiosugar nucleotide analogs: synthesis of 5'-(2,3,4-tri-O-acetyl-6-S-acetyl-6-thio-alpha-D-galactopyranosyl diphosphate).
abstract: The synthesis of a novel analog of uridine diphosphate galactose (UDP-Gal) is described. A sulfur atom was inserted into the 6-position of galactose to give uridine 5'-(2,3,4-tri-O-acetyl-6-S-acetyl-6-thio-alpha-D-galactopyranosyl diphosphate). This peracetylated thiol analogue of UDP-Gal has been synthesized in nine steps starting from methyl alpha-D-galactopyranoside in an overall yield of 3%.
authors.affiliation: Department of Medicinal Chemistry, College of Pharmacy, University of Michigan, Ann Arbor, MI 48109-1065, USA.
authors.forename: Jordan
authors.initials: J
authors.lastname: Elhalabi
authors.forename: Kevin G
authors.initials: KG
authors.lastname: Rice
mesh_terms: D000107:Acetylation; D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D005690:Galactose / Q000737:chemistry; D005700:Galactosyltransferases / Q000037:antagonists & inhibitors; D010766:Phosphorylation; D013862:Thiogalactosides / Q000138:chemical synthesis*; D014531:Uridine Diphosphate Galactose / Q000031:analogs & derivatives* / Q000138:chemical synthesis
chemical_list: D004791:Enzyme Inhibitors; D013862:Thiogalactosides; C475341:uridine 5'-(2,3,4-tri-O-acetyl-6-S-acetyl-6-thio-galactopyranosyl diphosphate); D014531:Uridine Diphosphate Galactose; D005700:Galactosyltransferases; D005690:Galactose