title: Synthesis of 1-(β-D-Galactopyranosyl)Thymine-6'-O-Triphosphate - A Potential Probe to Generate Reactive Dialdehyde for DNA-Enzyme Cross-Linking.
abstract: Concise, facile, and efficient synthesis of 1-(β-D-galactopyranosyl)thymine-6'-O-triphosphate, a potential probe that can generate reactive dialdehyde for DNA-enzyme cross-linking applications, was described starting from O,O'-bis(trimethylsilyl)thymine. Stannic chloride promoted glycosylation of 1,2,3,4,6-penta-O-acetyl-α-D-galactopyranose with O,O'-bis(trimethylsilyl)thymine, resulting in the formation of 1-(2,3,4,6-O-tetraacetyl-β-D-galactopyranosyl)thymine in 91% yield. Acetyl deprotection using methanolic ammonia afforded 1-(β-D-galactopyranosyl)thymine in 98% yield. The modified one-pot methodology was used to convert 1-(β-D-galactopyranosyl)thymine into 1-(β-D-galactopyranosyl)thymine-6'-O-triphosphate in 72% yield, which involves the formation of 1-(β-D-galactopyranosyl)thymine dichlorophosphoridate using POCl3 as the reagent at the monophosphorylation step followed by reaction with tributylammonium pyrophosphate and hydrolysis of resulting cyclic intermediate.
authors.affiliation: a Life Sciences Solutions Group, Thermo Fisher Scientific , Austin , Texas , USA.
authors.forename: Anilkumar R
authors.initials: AR
authors.lastname: Kore
authors.forename: Bo
authors.initials: B
authors.lastname: Yang
authors.forename: Balasubramanian
authors.initials: B
authors.lastname: Srinivasan
mesh_terms: D060326:Chemistry Techniques, Synthetic; D004247:DNA / Q000737:chemistry; D004798:Enzymes / Q000737:chemistry; D011122:Polyphosphates / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D004798:Enzymes; D011122:Polyphosphates; D004247:DNA; C005692:triphosphoric acid
keywords: Galactopyranosylthymine triphosphate; concise synthesis; nucleoside triphosphate; one-pot methodology; phosphorylation