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Reliable Synthesis of Various Nucleoside Diphosphate Glycopyranoses
Author(s) -
Wolf Saskia,
Zismann Tanja,
Lunau Nathalie,
Meier Chris
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200900572
Subject(s) - chemistry , nucleoside , cytidine , guanosine , fucose , nucleotide , moiety , nucleophile , stereochemistry , uridine , biochemistry , mannose , n acetylglucosamine , nucleotide salvage , galactosamine , glucosamine , galactose , enzyme , rna , gene , catalysis
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 cyclo Sal‐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 cyclo Sal 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 ‐ N Ac‐glucosamine, D ‐ N Ac‐galactosamine, D ‐fucose, L ‐fucose as well as 6‐deoxy‐ D ‐gulose were introduced.