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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

Jordan Elhalabi, Kevin G. Rice

Open publisher page 11 citations

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.

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What this paper is about

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.

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OpenAlex reports 11 citations for this work. Citation counts describe recorded attention and do not establish research quality.

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Available 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.

Key concepts: Galactosyltransferase, Uridine diphosphate, Thio-, Uridine, Glycosyltransferase, Chemistry, Substrate (aquarium), Nucleotide

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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 — Research Paper | ScholarLens