Micellar catalysis of the intramolecular aminolysis of the β‐lactam antibiotic cephaclor

Detalhes bibliográficos
Autor(a) principal: Oliveira, Anselmo G. [UNESP]
Data de Publicação: 1991
Outros Autores: Nothenberg, Michael S., Cuccovia, Iolanda M., Chaimovich, Hernan
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UNESP
Texto Completo: http://dx.doi.org/10.1002/poc.610040105
http://hdl.handle.net/11449/228202
Resumo: The rate of intramolecular degradation of cephaclor, involving the attack of the amino group at C‐17 (N‐18) on the β‐lactam carbonyl, was increased up to 50‐fold by neutral (polyoxyethylene‐23 lauryl ether; Brij) and zwitterionic [3‐(N‐dodecyl‐N, N‐dimethylammonium) propane 1‐sulphonate; (SDP)] micelles. The rate of OH− attack on cephaclor was increased 2–3‐fold by Brij and SDP micelles. In the absence of micelles the rate of intramolecular degradation of cephaclor increased by up to 2‐fold by addition of organic solvents. Distance calculations, based on the crystal structure of the antibiotic, showed that the intramolecular degration can only proceed in a conformation involving a cis‐amide bond (N‐14—C‐15). Micellar catalysis of the intramolecular degradation process was proposed to be due to the stabilization of the reactive conformation. Copyright © 1991 John Wiley & Sons Ltd.
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spelling Micellar catalysis of the intramolecular aminolysis of the β‐lactam antibiotic cephaclorThe rate of intramolecular degradation of cephaclor, involving the attack of the amino group at C‐17 (N‐18) on the β‐lactam carbonyl, was increased up to 50‐fold by neutral (polyoxyethylene‐23 lauryl ether; Brij) and zwitterionic [3‐(N‐dodecyl‐N, N‐dimethylammonium) propane 1‐sulphonate; (SDP)] micelles. The rate of OH− attack on cephaclor was increased 2–3‐fold by Brij and SDP micelles. In the absence of micelles the rate of intramolecular degradation of cephaclor increased by up to 2‐fold by addition of organic solvents. Distance calculations, based on the crystal structure of the antibiotic, showed that the intramolecular degration can only proceed in a conformation involving a cis‐amide bond (N‐14—C‐15). Micellar catalysis of the intramolecular degradation process was proposed to be due to the stabilization of the reactive conformation. Copyright © 1991 John Wiley & Sons Ltd.Departamento de Farmacos e Medicamentos Faculdade de Ciências Farmaceuticas-UNESP, Araraquara, São PauloFaculdade de Ciências Farmaceuticas-Usp, São PauloDepartamento de Bioquimica Instituto de Quimica Universidade de São Paulo, Caixa Postal CEP 01498, São Paulo, 20780Departamento de Farmacos e Medicamentos Faculdade de Ciências Farmaceuticas-UNESP, Araraquara, São PauloUniversidade Estadual Paulista (UNESP)Universidade de São Paulo (USP)Oliveira, Anselmo G. [UNESP]Nothenberg, Michael S.Cuccovia, Iolanda M.Chaimovich, Hernan2022-04-29T07:51:56Z2022-04-29T07:51:56Z1991-01-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article19-24http://dx.doi.org/10.1002/poc.610040105Journal of Physical Organic Chemistry, v. 4, n. 1, p. 19-24, 1991.1099-13950894-3230http://hdl.handle.net/11449/22820210.1002/poc.6100401052-s2.0-84986927409Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengJournal of Physical Organic Chemistryinfo:eu-repo/semantics/openAccess2024-06-24T13:45:38Zoai:repositorio.unesp.br:11449/228202Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T17:20:02.201544Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false
dc.title.none.fl_str_mv Micellar catalysis of the intramolecular aminolysis of the β‐lactam antibiotic cephaclor
title Micellar catalysis of the intramolecular aminolysis of the β‐lactam antibiotic cephaclor
spellingShingle Micellar catalysis of the intramolecular aminolysis of the β‐lactam antibiotic cephaclor
Oliveira, Anselmo G. [UNESP]
title_short Micellar catalysis of the intramolecular aminolysis of the β‐lactam antibiotic cephaclor
title_full Micellar catalysis of the intramolecular aminolysis of the β‐lactam antibiotic cephaclor
title_fullStr Micellar catalysis of the intramolecular aminolysis of the β‐lactam antibiotic cephaclor
title_full_unstemmed Micellar catalysis of the intramolecular aminolysis of the β‐lactam antibiotic cephaclor
title_sort Micellar catalysis of the intramolecular aminolysis of the β‐lactam antibiotic cephaclor
author Oliveira, Anselmo G. [UNESP]
author_facet Oliveira, Anselmo G. [UNESP]
Nothenberg, Michael S.
Cuccovia, Iolanda M.
Chaimovich, Hernan
author_role author
author2 Nothenberg, Michael S.
Cuccovia, Iolanda M.
Chaimovich, Hernan
author2_role author
author
author
dc.contributor.none.fl_str_mv Universidade Estadual Paulista (UNESP)
Universidade de São Paulo (USP)
dc.contributor.author.fl_str_mv Oliveira, Anselmo G. [UNESP]
Nothenberg, Michael S.
Cuccovia, Iolanda M.
Chaimovich, Hernan
description The rate of intramolecular degradation of cephaclor, involving the attack of the amino group at C‐17 (N‐18) on the β‐lactam carbonyl, was increased up to 50‐fold by neutral (polyoxyethylene‐23 lauryl ether; Brij) and zwitterionic [3‐(N‐dodecyl‐N, N‐dimethylammonium) propane 1‐sulphonate; (SDP)] micelles. The rate of OH− attack on cephaclor was increased 2–3‐fold by Brij and SDP micelles. In the absence of micelles the rate of intramolecular degradation of cephaclor increased by up to 2‐fold by addition of organic solvents. Distance calculations, based on the crystal structure of the antibiotic, showed that the intramolecular degration can only proceed in a conformation involving a cis‐amide bond (N‐14—C‐15). Micellar catalysis of the intramolecular degradation process was proposed to be due to the stabilization of the reactive conformation. Copyright © 1991 John Wiley & Sons Ltd.
publishDate 1991
dc.date.none.fl_str_mv 1991-01-01
2022-04-29T07:51:56Z
2022-04-29T07:51:56Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://dx.doi.org/10.1002/poc.610040105
Journal of Physical Organic Chemistry, v. 4, n. 1, p. 19-24, 1991.
1099-1395
0894-3230
http://hdl.handle.net/11449/228202
10.1002/poc.610040105
2-s2.0-84986927409
url http://dx.doi.org/10.1002/poc.610040105
http://hdl.handle.net/11449/228202
identifier_str_mv Journal of Physical Organic Chemistry, v. 4, n. 1, p. 19-24, 1991.
1099-1395
0894-3230
10.1002/poc.610040105
2-s2.0-84986927409
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Journal of Physical Organic Chemistry
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 19-24
dc.source.none.fl_str_mv Scopus
reponame:Repositório Institucional da UNESP
instname:Universidade Estadual Paulista (UNESP)
instacron:UNESP
instname_str Universidade Estadual Paulista (UNESP)
instacron_str UNESP
institution UNESP
reponame_str Repositório Institucional da UNESP
collection Repositório Institucional da UNESP
repository.name.fl_str_mv Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)
repository.mail.fl_str_mv
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