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J Am Chem Soc. 2012 Apr 11;134(14):6120-3. doi: 10.1021/ja301566t. Epub 2012 Mar 30.

Site-selective bromination of vancomycin.

Author information

1
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, USA.

Abstract

We report the site-selective bromination of vancomycin to produce, with substantial efficiency, previously unknown monobromovancomycins, a dibromovancomycin, and a tribromovancomycin. We document the inherent reactivity of native vancomycin toward N-bromophthalimide. We then demonstrate significant rate acceleration and perturbation of the inherent product distribution in the presence of a rationally designed peptide-based promoter. Alternative site selectivity is observed as a function of solvent and replacement of the peptide with guanidine.

PMID:
22462775
PMCID:
PMC3327726
DOI:
10.1021/ja301566t
[Indexed for MEDLINE]
Free PMC Article

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