Journal
CARBOHYDRATE RESEARCH
Volume 337, Issue 21-23, Pages 2187-2194Publisher
ELSEVIER SCI LTD
DOI: 10.1016/S0008-6215(02)00183-0
Keywords
GalN-1-P; acylamidosugars; UDP-sugars; morpholidate coupling; diazo transfer
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UDP-GalNAc analogues with slight modifications in the 2-acetamido group of the GalNAc moiety are prepared in order to study their role in the mechanism of the N-acetylgalactosaminyl transferase mediated glycosylation step. The analogues with N-propionyl, N-butyryl- and N-bromoacetyl-groups were synthesized, utilizing Khorana's morpholidate coupling method starting from D-galactosaminyl-l-phosphate after selective N-acylation of its amino group with the appropriate N-acyloxysuccinimides. Furthermore. in addition to UDP-galactosamine its 2-azido analogue has been efficiently prepared involving a metal catalyzed diazo transfer reaction. (C) 2002 Elsevier Science Ltd. All rights reserved.
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