From Amino Acids to Nature-Inspired Molecular Scaffolds: Incorporation of Medium-Sized Bridged Heterocycles into a Peptide Backbone

Autores
la Venia, Agustina; Ventosa Andres, Pilar; Hradilova, Ludmila; Krchnak, Viktor
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Novel molecular scaffolds comprising two to four bridged and fused heterocycles were synthesized from amino acids using seven-membered endocyclic N-acyliminium ions as key intermediates in acid-mediated tandem reactions with internal nucleophiles. This complexity-generating synthesis proceeds with high efficiency and with full stereocontrol of the newly generated stereogenic center. These results have extended the scope of medium-sized cyclic iminium ion chemistry, making it applicable as a regio- and stereoselective synthetic strategy for the generation of complex polycyclic structures. Furthermore, its compatibility with the traditional Merrifield synthesis of peptides on solid supports allowed the incorporation of the previously unexplored conformationally restricted cyclic systems into peptides without a need to independently synthesize the scaffold
Fil: la Venia, Agustina. Palacky University; República Checa. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Ventosa Andres, Pilar. Palacky University; República Checa
Fil: Hradilova, Ludmila. Klášterní Hradisko; República Checa
Fil: Krchnak, Viktor. Palacky University; República Checa. University of Notre Dame; Estados Unidos
Materia
Medium-Sized Iminiums
Medium-Sized Bridged Heterobicycles
Regio- And Stereoselectivity
Peptidomimetics
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:11336/29743
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/29743
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling From Amino Acids to Nature-Inspired Molecular Scaffolds: Incorporation of Medium-Sized Bridged Heterocycles into a Peptide Backbonela Venia, AgustinaVentosa Andres, PilarHradilova, LudmilaKrchnak, ViktorMedium-Sized IminiumsMedium-Sized Bridged HeterobicyclesRegio- And StereoselectivityPeptidomimeticshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Novel molecular scaffolds comprising two to four bridged and fused heterocycles were synthesized from amino acids using seven-membered endocyclic N-acyliminium ions as key intermediates in acid-mediated tandem reactions with internal nucleophiles. This complexity-generating synthesis proceeds with high efficiency and with full stereocontrol of the newly generated stereogenic center. These results have extended the scope of medium-sized cyclic iminium ion chemistry, making it applicable as a regio- and stereoselective synthetic strategy for the generation of complex polycyclic structures. Furthermore, its compatibility with the traditional Merrifield synthesis of peptides on solid supports allowed the incorporation of the previously unexplored conformationally restricted cyclic systems into peptides without a need to independently synthesize the scaffoldFil: la Venia, Agustina. Palacky University; República Checa. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Ventosa Andres, Pilar. Palacky University; República ChecaFil: Hradilova, Ludmila. Klášterní Hradisko; República ChecaFil: Krchnak, Viktor. Palacky University; República Checa. University of Notre Dame; Estados UnidosAmerican Chemical Society2014-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/29743la Venia, Agustina; Ventosa Andres, Pilar; Hradilova, Ludmila; Krchnak, Viktor; From Amino Acids to Nature-Inspired Molecular Scaffolds: Incorporation of Medium-Sized Bridged Heterocycles into a Peptide Backbone; American Chemical Society; Journal of Organic Chemistry; 79; 21; 10-2014; 10378-103890022-3263CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/jo501983jinfo:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/10.1021/jo501983jinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:38:05Zoai:ri.conicet.gov.ar:11336/29743instacron: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 09:38:05.771CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv From Amino Acids to Nature-Inspired Molecular Scaffolds: Incorporation of Medium-Sized Bridged Heterocycles into a Peptide Backbone
title From Amino Acids to Nature-Inspired Molecular Scaffolds: Incorporation of Medium-Sized Bridged Heterocycles into a Peptide Backbone
spellingShingle From Amino Acids to Nature-Inspired Molecular Scaffolds: Incorporation of Medium-Sized Bridged Heterocycles into a Peptide Backbone
la Venia, Agustina
Medium-Sized Iminiums
Medium-Sized Bridged Heterobicycles
Regio- And Stereoselectivity
Peptidomimetics
title_short From Amino Acids to Nature-Inspired Molecular Scaffolds: Incorporation of Medium-Sized Bridged Heterocycles into a Peptide Backbone
title_full From Amino Acids to Nature-Inspired Molecular Scaffolds: Incorporation of Medium-Sized Bridged Heterocycles into a Peptide Backbone
title_fullStr From Amino Acids to Nature-Inspired Molecular Scaffolds: Incorporation of Medium-Sized Bridged Heterocycles into a Peptide Backbone
title_full_unstemmed From Amino Acids to Nature-Inspired Molecular Scaffolds: Incorporation of Medium-Sized Bridged Heterocycles into a Peptide Backbone
title_sort From Amino Acids to Nature-Inspired Molecular Scaffolds: Incorporation of Medium-Sized Bridged Heterocycles into a Peptide Backbone
dc.creator.none.fl_str_mv la Venia, Agustina
Ventosa Andres, Pilar
Hradilova, Ludmila
Krchnak, Viktor
author la Venia, Agustina
author_facet la Venia, Agustina
Ventosa Andres, Pilar
Hradilova, Ludmila
Krchnak, Viktor
author_role author
author2 Ventosa Andres, Pilar
Hradilova, Ludmila
Krchnak, Viktor
author2_role author
author
author
dc.subject.none.fl_str_mv Medium-Sized Iminiums
Medium-Sized Bridged Heterobicycles
Regio- And Stereoselectivity
Peptidomimetics
topic Medium-Sized Iminiums
Medium-Sized Bridged Heterobicycles
Regio- And Stereoselectivity
Peptidomimetics
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Novel molecular scaffolds comprising two to four bridged and fused heterocycles were synthesized from amino acids using seven-membered endocyclic N-acyliminium ions as key intermediates in acid-mediated tandem reactions with internal nucleophiles. This complexity-generating synthesis proceeds with high efficiency and with full stereocontrol of the newly generated stereogenic center. These results have extended the scope of medium-sized cyclic iminium ion chemistry, making it applicable as a regio- and stereoselective synthetic strategy for the generation of complex polycyclic structures. Furthermore, its compatibility with the traditional Merrifield synthesis of peptides on solid supports allowed the incorporation of the previously unexplored conformationally restricted cyclic systems into peptides without a need to independently synthesize the scaffold
Fil: la Venia, Agustina. Palacky University; República Checa. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Ventosa Andres, Pilar. Palacky University; República Checa
Fil: Hradilova, Ludmila. Klášterní Hradisko; República Checa
Fil: Krchnak, Viktor. Palacky University; República Checa. University of Notre Dame; Estados Unidos
description Novel molecular scaffolds comprising two to four bridged and fused heterocycles were synthesized from amino acids using seven-membered endocyclic N-acyliminium ions as key intermediates in acid-mediated tandem reactions with internal nucleophiles. This complexity-generating synthesis proceeds with high efficiency and with full stereocontrol of the newly generated stereogenic center. These results have extended the scope of medium-sized cyclic iminium ion chemistry, making it applicable as a regio- and stereoselective synthetic strategy for the generation of complex polycyclic structures. Furthermore, its compatibility with the traditional Merrifield synthesis of peptides on solid supports allowed the incorporation of the previously unexplored conformationally restricted cyclic systems into peptides without a need to independently synthesize the scaffold
publishDate 2014
dc.date.none.fl_str_mv 2014-10
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/11336/29743
la Venia, Agustina; Ventosa Andres, Pilar; Hradilova, Ludmila; Krchnak, Viktor; From Amino Acids to Nature-Inspired Molecular Scaffolds: Incorporation of Medium-Sized Bridged Heterocycles into a Peptide Backbone; American Chemical Society; Journal of Organic Chemistry; 79; 21; 10-2014; 10378-10389
0022-3263
CONICET Digital
CONICET
url http://hdl.handle.net/11336/29743
identifier_str_mv la Venia, Agustina; Ventosa Andres, Pilar; Hradilova, Ludmila; Krchnak, Viktor; From Amino Acids to Nature-Inspired Molecular Scaffolds: Incorporation of Medium-Sized Bridged Heterocycles into a Peptide Backbone; American Chemical Society; Journal of Organic Chemistry; 79; 21; 10-2014; 10378-10389
0022-3263
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/jo501983j
info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/10.1021/jo501983j
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 American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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
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score 13.070432

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