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Site-selective bromination of vancomycin.

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.

SUBMITTER: Pathak TP

PROVIDER: S-EPMC3327726 | biostudies-literature | 2012 Apr

REPOSITORIES: biostudies-literature

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Site-selective bromination of vancomycin.

Pathak Tejas P TP Miller Scott J SJ

Journal of the American Chemical Society 20120330 14

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 solve ...[more]

PMID: 22462775

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