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.