A Programmable One-Pot Oligosaccharide Synthesis for Diversifying the Sugar Domains of Natural Products: A Case Study of Vancomycin

The notoriously difficult glycosylation of vancomycin was tackled in a one‐pot procedure. A number of oligosaccharides were synthesized and attached to the vancomycin aglycon to create a library of derivatives (see formula) to probe the effect of glycosylation on the antibiotic activity.

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2003-10, Vol.42 (38), p.4657-4660
Main Authors: Ritter, Thomas K., Mong, Kwok-Kong T., Liu, Haitian, Nakatani, Takuji, Wong, Chi-Huey
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
antibiotics
Biological Products - chemical synthesis
Biological Products - chemistry
carbohydrates
Glycosylation
Molecular Structure
Nitrogen - chemistry
oligosaccharides
Oligosaccharides - chemical synthesis
Oligosaccharides - chemistry
vancomycin
Vancomycin - analogs & derivatives
Vancomycin - chemical synthesis
Vancomycin - chemistry
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Description
Summary:The notoriously difficult glycosylation of vancomycin was tackled in a one‐pot procedure. A number of oligosaccharides were synthesized and attached to the vancomycin aglycon to create a library of derivatives (see formula) to probe the effect of glycosylation on the antibiotic activity.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200351534