Artificial N-functionalized UDP-glucosamine analogues as modified substrates for N-acetylglucosaminyl transferases

摘要

Analogues of UDP-GlcNAc modified at the 2-acetamido group of the GlcNAc moiety were prepared in order to study their role in the mechanism of N-acetylglucosaminyl transferase mediated glycosylation reactions.The structural analogues with N-formyl-,N-propionyl-,N-butyryl- and N-isobutyryl-groups were synthesized,utilizing the morpholidate coupling method starting from D-glucosaminyl-1-phosphate after selective N-acylation of its amino group with the appropriate N-acyloxysuccinimide esters as well as a chlorinated formylformiate.