Reliable Synthesis of Various Nucleoside Diphosphate Glycopyranoses |
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Authors: | Saskia Wolf Dipl.‐Chem. Tanja Zismann Dipl.‐Chem. Nathalie Lunau Dipl.‐Chem. Chris Meier Prof. Dr. |
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Affiliation: | 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 20 – 45 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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Keywords: | glycophosphotransferases glycosylation nucleotide sugars sugar conjugates |
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