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Gewählte Publikation:

Graziani, A; Zamyatina, A; Kosma, P.
(2004): A convenient synthesis of GDP D-glycero-alpha-D-manno-heptopyranose.
Carbohydr Res. 2004; 339(1):147-151 FullText FullText_BOKU

Abstract:
GDP D-glycero-alpha-D-manno-Heptopyranose has been prepared in good overall yield from 2,3,4,6,7-penta-O-acetyl-D-glycero-D-manno-heptopyranose by a short-step synthesis. Phosphitylation using the phosphoramidite procedure afforded the alpha-anomer in high selectivity. Subsequent oxidation and partial deprotection gave the acetylated phosphate derivative, which was subjected to the coupling reaction with GMP-morpholidate to furnish the acetylated heptose nucleoside diphosphate in good yield. De-O-acetylation and final purification afforded the target GDP D-glycero-alpha-D-manno-heptopyranose, which serves as the substrate of the heptosyl transferase in Aneurinibacillus thermoaerophilus DSM 10155 and occurs as an intermediate in the biosynthesis of GDP 6-deoxy-heptose in Yersinia pseudotuberculosis. (C) 2003 Elsevier Ltd. All rights reserved.
Autor/innen der BOKU Wien:
Kosma Paul
Zamyatina Alla
BOKU Gendermonitor:

Find related publications in this database (using NML MeSH Indexing)
Acetylation -
Bacillaceae - metabolism
Diphosphates - chemistry
Glycoproteins - chemistry
Guanosine Diphosphate - chemistry
Heptoses - chemical synthesis
Lipopolysaccharides - chemistry
Magnetic Resonance Spectroscopy - chemistry
Models, Chemical - chemistry
Organophosphorus Compounds - chemistry
Oxidation-Reduction - chemistry
Yersinia pseudotuberculosis - metabolism

Find related publications in this database (Keywords)
heptose
GDP-heptose
sugar nucleotide
lipopolysaccharide
surface-layer glycoprotein


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