Reliable synthesis of various nucleoside diphosphate glycopyranoses.
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.
Wolf
Saskia
S
Organic Chemistry, Department of Chemistry, Faculty of Science, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany.
Zismann
Tanja
T
Lunau
Nathalie
N
Meier
Chris
C
D005690:Galactose / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D005947:Glucose / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D006031:Glycosylation; D016695:Glycosyltransferases / Q000378:metabolism; D006601:Hexoses / Q000138:chemical synthesis / Q000737:chemistry; D008358:Mannose / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D009702:Nucleoside Diphosphate Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D009713:Nucleotidyltransferases / Q000378:metabolism*
D006601:Hexoses; D009005:Monosaccharides; D009702:Nucleoside Diphosphate Sugars; C057406:gulose; D016695:Glycosyltransferases; D009713:Nucleotidyltransferases; D005947:Glucose; D008358:Mannose; D005690:Galactose