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Bioorganic & medicinal chemistry letters

Synthesis and biological evaluation of penem inhibitors of bacterial signal peptidase.


PMID 19427205

Abstract

We report the first synthesis of a 5S penem, known to bind bacterial type I signal peptidase, from the commercially available and inexpensive 6-aminopenicillanic acid. We report the first in vivo activity of the compound and use structure-activity relationship studies to begin to define the determinants of signal peptidase binding and also to begin to optimize the penem as an antibiotic.

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A70909
(+)-6-Aminopenicillanic acid, 96%
C8H12N2O3S