Article (Scientific journals)
Effects of nucleophiles on the breakdown of the benzylpenicilloyl-enzyme complex EI formed between benzylpenicillin and the exocellular DD-carboxypeptidase--transpeptiase of Streptomyces strain R61
Marquet, Alberto; Frère, Jean-Marie; Ghuysen, Jean-Marie et al.
1979In Biochemical Journal, 177 (3), p. 909-916
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Keywords :
alcohols/pharmacology; amines/pharmacology; carboxypeptidases/*metabolism; chemical Phenomena; chemistry; glycerol/pharmacology; hydroxylamines/pharmacology; muramoylpentapeptide carboxypeptidase/*metabolism; penicillin g/*metabolism; peptides/pharmacology; serine/metabolism; streptomyces/*enzymology
Abstract :
[en] Serine is one of the enzyme residues with which benzylpenicillin collides as a result of its binding to the Streptomyces strain-R61 DD-carboxypeptidase-transpeptidase enzyme. Nucleophilic attack occurs on C(7) of the bound antibiotic molecule with formation of a benzylpenicilloyl-serine ester linkage, i.e. formation of the benzylpenicilloyl-enzyme EI complex. To reject the bound penicilloyl moiety and consequently to recover its initial activities, the strain-R61 enzyme has developed two possible mechanisms. Pathway A is a direct attack of the serine ester linkage by an exogenous nucleophile, resulting in the transfer of the benzylpenicilloyl moiety to this nucleophile. In pathway B, the benzylpenicilloyl moiety is first fragmented by C(5)-C(6) cleavage and the enzyme-bound phenylacetylglycyl residue thus produced is in turn transferred to the nucleophile. Pathway B occurs with water, glycylglycine and other amino compounds. Both pathways A and B occur with glycerol, other ROH nucleophiles and neutral hydroxylamine. The nucleophilic attacks are enzyme-catalysed.
Disciplines :
Biochemistry, biophysics & molecular biology
Microbiology
Author, co-author :
Marquet, Alberto;  Université de Liège - ULiège > Institut de Botanique > Service de Microbiologie
Frère, Jean-Marie ;  Université de Liège - ULiège > Institut de Botanique > Service de Microbiologie
Ghuysen, Jean-Marie ;  Université de Liège - ULiège > Institut de Botanique > Service de Microbiologie
Loffet, Albert;  UCB
Language :
English
Title :
Effects of nucleophiles on the breakdown of the benzylpenicilloyl-enzyme complex EI formed between benzylpenicillin and the exocellular DD-carboxypeptidase--transpeptiase of Streptomyces strain R61
Publication date :
01 March 1979
Journal title :
Biochemical Journal
ISSN :
0264-6021
eISSN :
1470-8728
Publisher :
Portland Press, London, United Kingdom
Volume :
177
Issue :
3
Pages :
909-916
Peer reviewed :
Peer Reviewed verified by ORBi
Funders :
NIH - National Institutes of Health [US-MD]
Available on ORBi :
since 26 May 2011

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