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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Galactose / analogs & derivatives
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Galactose / chemical synthesis
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Galactose / chemistry
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Glucose / analogs & derivatives
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Glucose / chemical synthesis
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Glucose / chemistry
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Glycosylation
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Glycosyltransferases / metabolism
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Hexoses / chemical synthesis
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Hexoses / chemistry
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Mannose / analogs & derivatives
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Mannose / chemical synthesis
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Mannose / chemistry
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Monosaccharides / chemical synthesis*
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Monosaccharides / chemistry
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Nucleoside Diphosphate Sugars / chemical synthesis*
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Nucleoside Diphosphate Sugars / chemistry
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Nucleotidyltransferases / metabolism*
Substances
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Hexoses
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Monosaccharides
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Nucleoside Diphosphate Sugars
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gulose
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Glycosyltransferases
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Nucleotidyltransferases
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Glucose
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Mannose
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Galactose