Synthesis of uridine 5'-[2-S-pyridyl-3-thio-alpha-D-galactopyranosyl diphosphate]: precursor of UDP-thiogal sugar nucleotide donor substrate for beta-1,4-galactosyltransferase.
The syntheses of a novel uridine diphosphate galactose (UDP-Gal) analog, (UDP-2,4,6-tri-O-acetyl-3-S-acetyl-3-thio-alpha-D-galactopyranose) (11) and the thiolpyridine protected (Uridine 5'-[3-S-(2-S-pyridyl)-3-thio-alpha-D-galactopyranosyl diphosphate) analog (12) are described. The reported synthesis relies on the novel use of thiolpyridine to generate 12 which is a suitably protected intermediate for generating a UDP-thioGal derivative by reduction prior to enzyme transfer via beta-1,4-galactosyltransferase.
Elhalabi
Jordan
J
Department of Medicinal Chemistry, College of Pharmacy, University of Michigan, Ann Arbor, Michigan, USA.
Rice
Kevin G
KG
D009682:Magnetic Resonance Spectroscopy; D009237:N-Acetyllactosamine Synthase / Q000378:metabolism*; D014531:Uridine Diphosphate Galactose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism
D014531:Uridine Diphosphate Galactose; D009237:N-Acetyllactosamine Synthase