Journal of the American Chemical Society 2012-04-11

Site-selective bromination of vancomycin.

Tejas P Pathak, Scott J Miller

Index: J. Am. Chem. Soc. 134(14) , 6120-3, (2012)

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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.© 2012 American Chemical Society