Solid-phase synthesis of fused 1,4-diazepanone peptidomimetics via tandem N-iminium ion cyclization-nucleophilic addition

Autores
Ventosa Andrés, Pilar; Barea Ripoll, Carlos Alfonso; la Venia, Agustina; Krchnak, Viktor
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
We herein describe the solid-phase synthesis of protected N-oxoalkyl-derivatized peptides designed for subsequent acid-mediated, tandem N-acyliminium ion cyclization-nucleophilic addition reaction. The target compounds contained fused 1,4-diazepanones incorporated into a peptide backbone and served as conformational constraints. The scope and limitation of the ring formation were studied, and the structural requirements and reaction conditions for cyclization are outlined.
Fil: Ventosa Andrés, Pilar. University of Palacky; República Checa
Fil: Barea Ripoll, Carlos Alfonso. University of Palacky; República Checa
Fil: la Venia, Agustina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. University of Palacky; República Checa
Fil: Krchnak, Viktor. University of Palacky; República Checa. University of Notre Dame; Estados Unidos
Materia
1,4-Diazepan-2-One
1,4-Diazepan-5-One
Bisheterocycles
Iminium Chemistry
Seven-Membered Ring
Solid-Phase Synthesis
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/50237
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/50237
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Solid-phase synthesis of fused 1,4-diazepanone peptidomimetics via tandem N-iminium ion cyclization-nucleophilic additionVentosa Andrés, PilarBarea Ripoll, Carlos Alfonsola Venia, AgustinaKrchnak, Viktor1,4-Diazepan-2-One1,4-Diazepan-5-OneBisheterocyclesIminium ChemistrySeven-Membered RingSolid-Phase Synthesishttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1We herein describe the solid-phase synthesis of protected N-oxoalkyl-derivatized peptides designed for subsequent acid-mediated, tandem N-acyliminium ion cyclization-nucleophilic addition reaction. The target compounds contained fused 1,4-diazepanones incorporated into a peptide backbone and served as conformational constraints. The scope and limitation of the ring formation were studied, and the structural requirements and reaction conditions for cyclization are outlined.Fil: Ventosa Andrés, Pilar. University of Palacky; República ChecaFil: Barea Ripoll, Carlos Alfonso. University of Palacky; República ChecaFil: la Venia, Agustina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. University of Palacky; República ChecaFil: Krchnak, Viktor. University of Palacky; República Checa. University of Notre Dame; Estados UnidosPergamon-Elsevier Science Ltd2015-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/50237Ventosa Andrés, Pilar; Barea Ripoll, Carlos Alfonso; la Venia, Agustina; Krchnak, Viktor; Solid-phase synthesis of fused 1,4-diazepanone peptidomimetics via tandem N-iminium ion cyclization-nucleophilic addition; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 56; 40; 9-2015; 5424-54280040-4039CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2015.08.015info:eu-repo/semantics/altIdentifier/url/https://linkinghub.elsevier.com/retrieve/pii/S0040403915012964info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:43:08Zoai:ri.conicet.gov.ar:11336/50237instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 09:43:08.303CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Solid-phase synthesis of fused 1,4-diazepanone peptidomimetics via tandem N-iminium ion cyclization-nucleophilic addition
title Solid-phase synthesis of fused 1,4-diazepanone peptidomimetics via tandem N-iminium ion cyclization-nucleophilic addition
spellingShingle Solid-phase synthesis of fused 1,4-diazepanone peptidomimetics via tandem N-iminium ion cyclization-nucleophilic addition
Ventosa Andrés, Pilar
1,4-Diazepan-2-One
1,4-Diazepan-5-One
Bisheterocycles
Iminium Chemistry
Seven-Membered Ring
Solid-Phase Synthesis
title_short Solid-phase synthesis of fused 1,4-diazepanone peptidomimetics via tandem N-iminium ion cyclization-nucleophilic addition
title_full Solid-phase synthesis of fused 1,4-diazepanone peptidomimetics via tandem N-iminium ion cyclization-nucleophilic addition
title_fullStr Solid-phase synthesis of fused 1,4-diazepanone peptidomimetics via tandem N-iminium ion cyclization-nucleophilic addition
title_full_unstemmed Solid-phase synthesis of fused 1,4-diazepanone peptidomimetics via tandem N-iminium ion cyclization-nucleophilic addition
title_sort Solid-phase synthesis of fused 1,4-diazepanone peptidomimetics via tandem N-iminium ion cyclization-nucleophilic addition
dc.creator.none.fl_str_mv Ventosa Andrés, Pilar
Barea Ripoll, Carlos Alfonso
la Venia, Agustina
Krchnak, Viktor
author Ventosa Andrés, Pilar
author_facet Ventosa Andrés, Pilar
Barea Ripoll, Carlos Alfonso
la Venia, Agustina
Krchnak, Viktor
author_role author
author2 Barea Ripoll, Carlos Alfonso
la Venia, Agustina
Krchnak, Viktor
author2_role author
author
author
dc.subject.none.fl_str_mv 1,4-Diazepan-2-One
1,4-Diazepan-5-One
Bisheterocycles
Iminium Chemistry
Seven-Membered Ring
Solid-Phase Synthesis
topic 1,4-Diazepan-2-One
1,4-Diazepan-5-One
Bisheterocycles
Iminium Chemistry
Seven-Membered Ring
Solid-Phase Synthesis
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv We herein describe the solid-phase synthesis of protected N-oxoalkyl-derivatized peptides designed for subsequent acid-mediated, tandem N-acyliminium ion cyclization-nucleophilic addition reaction. The target compounds contained fused 1,4-diazepanones incorporated into a peptide backbone and served as conformational constraints. The scope and limitation of the ring formation were studied, and the structural requirements and reaction conditions for cyclization are outlined.
Fil: Ventosa Andrés, Pilar. University of Palacky; República Checa
Fil: Barea Ripoll, Carlos Alfonso. University of Palacky; República Checa
Fil: la Venia, Agustina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. University of Palacky; República Checa
Fil: Krchnak, Viktor. University of Palacky; República Checa. University of Notre Dame; Estados Unidos
description We herein describe the solid-phase synthesis of protected N-oxoalkyl-derivatized peptides designed for subsequent acid-mediated, tandem N-acyliminium ion cyclization-nucleophilic addition reaction. The target compounds contained fused 1,4-diazepanones incorporated into a peptide backbone and served as conformational constraints. The scope and limitation of the ring formation were studied, and the structural requirements and reaction conditions for cyclization are outlined.
publishDate 2015
dc.date.none.fl_str_mv 2015-09
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/50237
Ventosa Andrés, Pilar; Barea Ripoll, Carlos Alfonso; la Venia, Agustina; Krchnak, Viktor; Solid-phase synthesis of fused 1,4-diazepanone peptidomimetics via tandem N-iminium ion cyclization-nucleophilic addition; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 56; 40; 9-2015; 5424-5428
0040-4039
CONICET Digital
CONICET
url http://hdl.handle.net/11336/50237
identifier_str_mv Ventosa Andrés, Pilar; Barea Ripoll, Carlos Alfonso; la Venia, Agustina; Krchnak, Viktor; Solid-phase synthesis of fused 1,4-diazepanone peptidomimetics via tandem N-iminium ion cyclization-nucleophilic addition; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 56; 40; 9-2015; 5424-5428
0040-4039
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2015.08.015
info:eu-repo/semantics/altIdentifier/url/https://linkinghub.elsevier.com/retrieve/pii/S0040403915012964
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1844613357378732032
score 13.070432

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