Stereoselective synthesis of sugar nucleotides using neighboring group participation

A straightforward, efficient method for the chemical synthesis of sugar nucleotides derived from D-mannose and L-fucose precursors is described. This synthetic strategy involves the coupling of acylated glycosyl bromides with nucleoside 5'-diphosphates, which enables the exploitation of neighbo...

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Bibliographic Details
Published inCurrent protocols in nucleic acid chemistry Vol. Chapter 13; p. Unit 13.7
Main Authors Timmons, Shannon C, Jakeman, David L
Format Journal Article
LanguageEnglish
Published United States 01.12.2007
Subjects
Carbohydrates - chemistry
Chromatography, High Pressure Liquid
Magnetic Resonance Spectroscopy
Nucleotides - chemical synthesis
Stereoisomerism
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Summary:A straightforward, efficient method for the chemical synthesis of sugar nucleotides derived from D-mannose and L-fucose precursors is described. This synthetic strategy involves the coupling of acylated glycosyl bromides with nucleoside 5'-diphosphates, which enables the exploitation of neighboring group participation to exclusively prepare diastereomerically pure sugar nucleotides of desired 1,2-trans anomeric configuration. This is the first stereoselective direct coupling approach to sugar nucleotide synthesis. Following deprotection using triethylamine and purification via C18 reversed-phase ion-pair chromatography, UDP- and GDP-alpha-D-mannose as well as UDP- and GDP-beta-L-fucose were obtained in good yield in only four synthetic steps from D-mannose and L-fucose.
ISSN:1934-9289
DOI:10.1002/0471142700.nc1307s31