1215859-68-9Relevant academic research and scientific papers
Reliable synthesis of various nucleoside diphosphate glycopyranoses
Wolf, Saskia,Zismann, Tanja,Lunau, Nathalie,Meier, Chris
, p. 7656 - 7664 (2009)
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 pyranosyl1-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, thymi-dine, adenosine, 2′-deoxy-guanosine and 2′,3′-dideoxy-2′,3′- didehydrothymidine were used while the phosphates of D-glucose, D-galactose, D-mannose, DNAc-glucosamine, D-NAc-galactosamine, D-fucose, L-fucose as well as 6deoxy-D-gulose were introduced.
