Synthesis of uridine 5 '-[2-S-pyridy1-3-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 sy...

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Bibliographic Details
Published inNucleosides, nucleotides & nucleic acids Vol. 23; no. 1-2; pp. 195 - 205
Main Authors Elhalabi, J, Rice, KG
Format Journal Article
LanguageEnglish
Published PHILADELPHIA Taylor & Francis 01.01.2004
Subjects
Biochemistry & Molecular Biology
Life Sciences & Biomedicine
Magnetic Resonance Spectroscopy
N-Acetyllactosamine Synthase - metabolism
Science & Technology
Uridine Diphosphate Galactose - analogs & derivatives
Uridine Diphosphate Galactose - chemical synthesis
Uridine Diphosphate Galactose - chemistry
Uridine Diphosphate Galactose - metabolism
beta-1,4-galactosyltransferase
dithiodipyridine
thio sugars
OLIGOSACCHARIDES
GAL
ANALOGS
DIPHOSPHATE
thiopyridine derivatives
sugar nucleotides
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Summary: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.
Bibliography:Medline
NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1525-7770
1532-2335
DOI:10.1081/NCN-120027828