Selective derivatization of N-terminal cysteines using cyclopentenediones

The outcome of the Michael-type reaction between thiols and 2,2-disubstituted cyclopentenediones varies depending on the thiol. Stable compounds with two fused rings were formed upon reaction with 1,2-aminothiols (such as N-terminal cysteines in peptides). Other thiols gave reversibly Michael-type a...

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Detalles Bibliográficos
Autores: Brun Cubero, Omar, Agramunt, Jordi, Raich Armendáriz, Lluís Adrià, Rovira i Virgili, Carme, Pedroso Muller, Enrique, Grandas Sagarra, Anna
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2016
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/102811
Acceso en línea:https://hdl.handle.net/2445/102811
Access Level:acceso abierto
Palabra clave:Bioquímica
Reaccions químiques
Cisteïna
Biochemistry
Chemical reactions
Cysteine
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spelling Selective derivatization of N-terminal cysteines using cyclopentenedionesBrun Cubero, OmarAgramunt, JordiRaich Armendáriz, Lluís AdriàRovira i Virgili, CarmePedroso Muller, EnriqueGrandas Sagarra, AnnaBioquímicaReaccions químiquesCisteïnaBiochemistryChemical reactionsCysteineThe outcome of the Michael-type reaction between thiols and 2,2-disubstituted cyclopentenediones varies depending on the thiol. Stable compounds with two fused rings were formed upon reaction with 1,2-aminothiols (such as N-terminal cysteines in peptides). Other thiols gave reversibly Michael-type adducts that were in equilibrium with the starting materials. This differential reactivity allows differently placed cysteines to be distinguished and has been exploited to prepare bioconjugates incorporating two or three different moieties.American Chemical Society2016201720162016info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersion4 p.application/pdfhttps://hdl.handle.net/2445/102811Articles publicats en revistes (Química Inorgànica i Orgànica)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésVersió postprint del document publicat a: http://dx.doi.org/10.1021/acs.orglett.6b02301Organic Letters, 2016, vol. 18, num. 19, p. 4836-4839http://dx.doi.org/10.1021/acs.orglett.6b02301(c) American Chemical Society , 2016info:eu-repo/semantics/openAccessoai:recercat.cat:2445/1028112026-05-29T05:05:01Z
dc.title.none.fl_str_mv Selective derivatization of N-terminal cysteines using cyclopentenediones
title Selective derivatization of N-terminal cysteines using cyclopentenediones
spellingShingle Selective derivatization of N-terminal cysteines using cyclopentenediones
Brun Cubero, Omar
Bioquímica
Reaccions químiques
Cisteïna
Biochemistry
Chemical reactions
Cysteine
title_short Selective derivatization of N-terminal cysteines using cyclopentenediones
title_full Selective derivatization of N-terminal cysteines using cyclopentenediones
title_fullStr Selective derivatization of N-terminal cysteines using cyclopentenediones
title_full_unstemmed Selective derivatization of N-terminal cysteines using cyclopentenediones
title_sort Selective derivatization of N-terminal cysteines using cyclopentenediones
dc.creator.none.fl_str_mv Brun Cubero, Omar
Agramunt, Jordi
Raich Armendáriz, Lluís Adrià
Rovira i Virgili, Carme
Pedroso Muller, Enrique
Grandas Sagarra, Anna
author Brun Cubero, Omar
author_facet Brun Cubero, Omar
Agramunt, Jordi
Raich Armendáriz, Lluís Adrià
Rovira i Virgili, Carme
Pedroso Muller, Enrique
Grandas Sagarra, Anna
author_role author
author2 Agramunt, Jordi
Raich Armendáriz, Lluís Adrià
Rovira i Virgili, Carme
Pedroso Muller, Enrique
Grandas Sagarra, Anna
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Bioquímica
Reaccions químiques
Cisteïna
Biochemistry
Chemical reactions
Cysteine
topic Bioquímica
Reaccions químiques
Cisteïna
Biochemistry
Chemical reactions
Cysteine
description The outcome of the Michael-type reaction between thiols and 2,2-disubstituted cyclopentenediones varies depending on the thiol. Stable compounds with two fused rings were formed upon reaction with 1,2-aminothiols (such as N-terminal cysteines in peptides). Other thiols gave reversibly Michael-type adducts that were in equilibrium with the starting materials. This differential reactivity allows differently placed cysteines to be distinguished and has been exploited to prepare bioconjugates incorporating two or three different moieties.
publishDate 2016
dc.date.none.fl_str_mv 2016
2016
2016
2017
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/102811
url https://hdl.handle.net/2445/102811
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Versió postprint del document publicat a: http://dx.doi.org/10.1021/acs.orglett.6b02301
Organic Letters, 2016, vol. 18, num. 19, p. 4836-4839
http://dx.doi.org/10.1021/acs.orglett.6b02301
dc.rights.none.fl_str_mv (c) American Chemical Society , 2016
info:eu-repo/semantics/openAccess
rights_invalid_str_mv (c) American Chemical Society , 2016
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 4 p.
application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv Articles publicats en revistes (Química Inorgànica i Orgànica)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,198674

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