Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science

Design, Synthesis and Testing of Transition State Analogues of Alanine Racemase as Antibacterials

DK Leung, PR Andrews, DJ Craik, MN Iskander and DA Winkler

Australian Journal of Chemistry 38(2) 297 - 306
Published: 1985


Transition state analogues have been designed for alanine racemase , an important enzyme target for the development of bacterial cell wall inhibitors. These analogues are based on the transition state structure obtained from MINDO/3 calculations on the reaction pathway of a model alanine racemization . A number of analogues have been synthesized and are shown to have weak anti-bacterial activity, but results from microbiological assays indicate that their antibacterial activity is not due to inhibition of alanine racemase . Subsequent n.m.r .studies have shown that they are unstable in aqueous environments. Formaldehyde has been identified as one of the degradation products, and the likely source of antibacterial activity.

© CSIRO 1985

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