Correlation between hydrolysis of the -lactam bond of the cephalosporin nucleus and expulsion of the 3-substituent.

Journal of bacteriology ·Vol. 110 ·No. 3 ·1972-06-00 ·Pages 988-91

O'Callaghan CH, Kirby SM, Morris A, Waller RE, Duncombe RE

Abstract

The hydrolysis of two cephalosporins by three different beta-lactamases has been studied. Each enzyme caused a decrease in ultraviolet absorption, a loss of biological activity, and the release of the leaving group from the 3-position. The changes occurred at the same rate and to the same extent with each enzyme, and it is inferred that the loss of the leaving group is a consequence of, and not a prerequisite for, hydrolysis of the beta-lactam ring.

MeSH Terms

Absorption Autoanalysis Azides/biosynthesis Cephalosporins/metabolism Chemical Phenomena Chemistry Chromatography, Ion Exchange Enterobacter/enzymology Enterobacteriaceae/enzymology Escherichia coli/enzymology Hydrolysis Klebsiella/enzymology Penicillinase/isolation & purification,metabolism Pyridines/biosynthesis Spectrophotometry Ultraviolet Rays beta-Lactams/metabolism

Chemicals

Azides Cephalosporins Pyridines beta-Lactams Penicillinase

Authors & Affiliations

5 authors, click to expand affiliations / ORCID

O'Callaghan C H

Kirby S M

Morris A

Waller R E

Duncombe R E

References (6)

6 references, click to expand

Cephalosporinase and penicillinase activities of a beta-lactamase from Pseudomonas pyocyanea.
Biochem J. 1965 Sep;96(3):739-52 PMID: 5862414
Inhibition of beta-lactamase decomposition of cephaloridine and cephalothin by other cephalosporins.
Antimicrob Agents Chemother (Bethesda). 1966;6:337-43 PMID: 5183152
Effects of beta-lactamase from gram-negative organisms on cephalosporins and penicillins.
Antimicrob Agents Chemother (Bethesda). 1968;8:57-63 PMID: 5195741
Products of aminolysis and enzymic hydrolysis of the cephalosporins.
Biochem J. 1970 Feb;116(3):371-84 PMID: 5435685
A comparative study of eight distinct beta-lactamases synthesized by gram-negative bacteria.
J Gen Microbiol. 1970 Apr;61(1):43-61 PMID: 5489064
Novel method for detection of beta-lactamases by using a chromogenic cephalosporin substrate.
Antimicrob Agents Chemother. 1972 Apr;1(4):283-8 PMID: 4208895

Article Info

Journal

Journal of bacteriology

Abbr.

J Bacteriol

ISSN

0021-9193

DOI

10.1128/jb.110.3.988-991.1972

Published

1972-06-00

Pages

988-91

Language

English

Region

United States

NLM ID

2985120R

PMCID

PMC247519

Subset

External Links

PubMed source DOI: 10.1128/jb.110.3.988-991.1972 PMC Full Text View journal details

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Correlation between hydrolysis of the -lactam bond of the cephalosporin nucleus and expulsion of the 3-substituent.

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