Carbapenem biosynthesis: confirmation of stereochemical assignments and the role of CarC in the ring stereoinversion process from L-proline

A Stapon, R Li, CA Townsend

Index: Stapon, Anthony; Li, Rongfeng; Townsend, Craig A. Journal of the American Chemical Society, 2003 , vol. 125, # 28 p. 8486 - 8493

Full Text: HTML

Citation Number: 51

Abstract

(5 R)-Carbapen-2-em-3-carboxylic acid is the simplest structurally among the naturally occurring carbapenem β-lactam antibiotics. It co-occurs with two saturated (3 S, 5 S)-and (3 S, 5 R)-carbapenam carboxylic acids. Confusion persists in the literature about the signs of rotation and absolute configurations of these compounds that is resolved in this paper.(3 S, 5 S)-Carbapenam carboxylic acid was prepared from l-pyroglutamic acid to ...