Work

Effect of side-chain substitution of a CH2 group by sulfur on the antimicrobial activity of natural penicillins and cephalosporins.

Year: 1985

Type: article

Abstract: The S-carboxymethyl-D-cysteine side-chain analogs of cephalosporin C and deacetoxycephalosporin C were found to have markedly increased in vitro activity against Gram-positive and Gram-negative bacteria compared to the natural antibiotics. The S-carboxymethyl-L-cysteine analogs were less active than the S-carboxymethyl-D-cysteine analogs but against most organisms tested, still more active than the natural compounds. The effect of replacement of CH2 with S was less dramatic in the case of penicillin N and isopenicillin N. The S-carboxymethyl-D-cysteine analog of deacetoxycephalosporin C was found to be orally available in rats.

Source: The Journal of Antibiotics

DOI: 10.7164/antibiotics.38.1550

Authors: S. WOLFE, C. LÜBBE, S. E. JENSEN, H. HERNANDEZ, A. L. DEMAIN

Institutions: Queen's University, University of Alberta, Massachusetts Institute of Technology

Language: English

Topic: Synthesis of β-Lactam Compounds

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

SDG: Good health and well-being

Open Access status: bronze

Funders: National Science Foundation, Deutsche Forschungsgemeinschaft