Synthesis of Uridine 5′‐[2‐S‐Pyridyl‐3‐thio‐α‐d‐galactopyranosyl Diphosphate]: Precursors of UDP‐Thiogal Sugar Nucleotide Donor Substrate for β‐1,4‐Galactosyltransferase
- 1 January 2004
- journal article
- Published by Taylor & Francis in Nucleosides, Nucleotides and Nucleic Acids
- Vol. 23 (1-2) , 195-205
- https://doi.org/10.1081/ncn-120027828
Abstract
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.Keywords
This publication has 15 references indexed in Scilit:
- Thiosugar nucleotide analogs: Synthesis of 5′-(2,3,4-tri-O-acetyl-6-S-acetyl-6-thio-α-d-galactopyranosyl diphosphate)Carbohydrate Research, 2002
- Thiosugar nucleotide analogues: synthesis of uridine 5′-(2,3,6-tri-O-acetyl-4-S-acetyl-4-thio-α-d-galactopyranosyl diphosphate)Carbohydrate Research, 2001
- Glycosyltransferase structure and mechanismCurrent Opinion in Structural Biology, 2000
- Crystal structures of the bovine beta 4galactosyltransferase catalytic domain and its complex with uridine diphosphogalactoseThe EMBO Journal, 1999
- Novel aspects of interaction between UDP-Gal and GlcNAc β-1,4-Galactosyltransferase: Transferability and remarkable inhibitory activity of UDP-(mono-O-methylated Gal), UDP-Fuc and UDP-ManBioorganic & Medicinal Chemistry, 1996
- Synthesis of the carbocyclic analog of uridine 5′-(α-D-galactopyranosyl diphosphate) (UDP-Gal) as an inhibitor of β(1 → 4)-galactosyltransferaseCanadian Journal of Chemistry, 1995
- Synthesis of UDP-6-deoxy- and -6-fluoro-D-galactoses and their enzymatic glycosyl transfer to mono- and biantennary carbohydrate chainsTetrahedron Letters, 1993
- Chemical-enzymic synthesis of 5'-thio-N-acetyllactosamine: the first disaccharide with sulfur in the ring of the non-reducing sugarJournal of the American Chemical Society, 1992
- ASSEMBLY OF ASPARAGINE-LINKED OLIGOSACCHARIDESAnnual Review of Biochemistry, 1985
- 1,2:5,6-Di-O-isopropylidene-α-D-galactofuranoAustralian Journal of Chemistry, 1975