BOKU - Universität für Bodenkultur Wien - Forschungsinformationssystem
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
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- 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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