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Reliable Synthesis of Various Nucleoside Diphosphate Glycopyranoses

Authors

  • Saskia Wolf Dipl.-Chem.,

    1. Organic Chemistry, Department of Chemistry, Faculty of Science, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg (Germany), Fax: (+49) 40-42838-5592
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  • Tanja Zismann Dipl.-Chem.,

    1. Organic Chemistry, Department of Chemistry, Faculty of Science, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg (Germany), Fax: (+49) 40-42838-5592
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  • Nathalie Lunau Dipl.-Chem.,

    1. Organic Chemistry, Department of Chemistry, Faculty of Science, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg (Germany), Fax: (+49) 40-42838-5592
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  • Chris Meier Prof. Dr.

    1. Organic Chemistry, Department of Chemistry, Faculty of Science, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg (Germany), Fax: (+49) 40-42838-5592
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Abstract

A reliable and high yielding synthetic pathway for the synthesis of the biologically highly important class of nucleoside diphosphate sugars (NDP-sugars) was developed by using various cycloSal-nucleotides 1 and 9 as active ester building blocks. The reaction with anomerically pure pyranosyl-1-phosphates 2 led to the target NDP-sugars 2045 in a nucleophilic displacement reaction, which cleaves the cycloSal moiety in anomerically pure forms. As nucleosides cytidine, uridine, thymidine, adenosine, 2′-deoxy-guanosine and 2′,3′-dideoxy-2′,3′-didehydrothymidine were used while the phosphates of D-glucose, D-galactose, D-mannose, D-NAc-glucosamine, D-NAc-galactosamine, D-fucose, L-fucose as well as 6-deoxy-D-gulose were introduced.

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