Synthesis and biological activities of the (Z) isomers of carbapenem antibiotics
- 1 February 1983
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 26 (2) , 271-275
- https://doi.org/10.1021/jm00356a029
Abstract
Naturally occurring carbapenem antibiotics having a double bond in the side chain, when refluxed in chloroform containing quarternary alkylammonium halides, were converted into Z isomers in high yields. The mechanism of this new equilibrium involves intramolecular proton transfer from the carboxylic acid to the C .alpha. to the S atom in the side chain as shown by 2H-labeling experiments. Some Z isomers showed stronger protective effects in mice infected by Escherichia coli 0-111 and more potent synergistic activities with cefotiam in mice infected by Proteus vulgaris GN4815 than did the naturally occurring E isomers. The decomposition rates of the Z isomers in mouse kidney homogenates were .apprx. 3-fold slower than those of the E isomers.This publication has 2 references indexed in Scilit:
- C-19393 S2 and H2, new carbapenem antibiotics. IV. Inhibitory activity against .BETA.-lactamases.The Journal of Antibiotics, 1981
- C-19393 S2 and H2, new carbapenem antibiotics. II. Isolation and structures.The Journal of Antibiotics, 1980