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Letter

Stereoselective Chemical Synthesis of Sugar Nucleotides via Direct Displacement of Acylated Glycosyl Bromides

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Shannon C. Timmons^† and David L. Jakeman*^†^‡

Department of Chemistry, Dalhousie University, Halifax, N.S., Canada B3H 4J3, and College of Pharmacy, Dalhousie University, Halifax, N.S., Canada B3H 3J5

Org. Lett., 2007, 9 (7), pp 1227–1230

DOI: 10.1021/ol063068d

Publication Date (Web): March 6, 2007

†

Department of Chemistry.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

‡

College of Pharmacy.

, david.jakeman@dal.ca

Abstract

The use of Leloir glycosyltransferases to prepare biologically relevant oligosaccharides and glycoconjugates requires access to sugar nucleoside diphosphates, which are notoriously difficult to efficiently synthesize and purify. We report a novel stereoselective route to UDP- and GDP-α-d-mannose as well as UDP- and GDP-β-l-fucose via direct displacement of acylated glycosyl bromides with nucleoside 5‘-diphosphates.

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Published In Issue March 29, 2007
Received December 19, 2006

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Letter

Stereoselective Chemical Synthesis of Sugar Nucleotides via Direct Displacement of Acylated Glycosyl Bromides

Abstract

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History

Recommend & Share

Related Content

Exploiting Nucleotidylyltransferases To Prepare Sugar Nucleotides

Sonochemistry: A Powerful Way of Enhancing the Efficiency of Carbohydrate Synthesis

Rapid Chemical Synthesis of Sugar Nucleotides in a Form Suitable for Enzymic Oligosaccharide Synthesis

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