Non β-Lactam Analogs of Penicillins and Cephalosporins

  • Jacqueline Marchand-Brynaert
  • Léon Ghosez

Abstract

The remarkable biological effect of β-Iactam antibiotics results from their capacity to disrupt the biosynthesis of the bacterial cell wall. They do this by inhibiting D,D-transpeptidases, membranebound serine peptidases which are involved in the peptidoglycan cross-linking. The extensive use of penicillins and other β-Iactam antibiotics in medicine over the last forty years has given rise to an increasing number of resistant bacteria, a phenomenon mainly due to the production of β-Iactamases. Therefore, a current challenge in antibiotherapy is the production of new structures which will overcome the defense mechanisms of the bacteria. Non β-Iactams may provide a solution to this problem. In the last few years, several research groups have launched programmes to synthesise rationally-designed compounds which are not β-Iactams, but which hopefully inhibit the same enzymes. This review describes their efforts, successes and failures.

Keywords

MeOH Lactone Peptidoglycan Phosphite Methicillin 

Abbreviations

PBP

penicillin binding protein

PNB

para-nitro benzyl

PMB

para-methoxylbenzyl

TCE

trichloroethyl

PIV

pivaloyloxymethyl

EWG

electron-withdrawing group

FtN

phthalimido

Tos

tosyl

ATMO

2-(amino-4-thiazolyl)-2-(methoxy)-iminoacetyl

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Copyright information

© Springer-Verlag Berlin Heidelberg 1990

Authors and Affiliations

  • Jacqueline Marchand-Brynaert
    • 1
  • Léon Ghosez
    • 1
  1. 1.Laboratoire de Chimie Organique de SynthéseUniversité Catholique de LouvainLouvain-La-NeuveBelgium

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