Polymer-Supported Stereoselective Synthesis of Tetrahydro-2H-oxazolo[3,2-a]pyrazin-5(3H)-ones from N-(2-Oxo-ethyl)-Derivatized Dipeptides via Eastbound Iminiums

Autores
la Venia, Agustina; Dolensky, Bohumil; Krchnak, Viktor
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Polymer-supported N-(2-oxo-ethyl)-derivatized Ser/Thr/Cys-containing dipeptides were synthesized and subjected to acid-mediated tandem N-acylium ion cyclization−nucleophilic addition to yield tetrahydro-2H-oxazolo- [3,2-a]pyrazin-5(3H)-ones. The reaction conditions and building-block combinations for stereoselective synthesis of the newly formed asymmetric carbon were developed. The synthesis was fully compatible with solid-phase peptide synthesis, and the products serve as conformationally constrained peptidomimetics. The traceless synthesis of bicycles is also reported as part of this work.
Fil: la Venia, Agustina. Palacký University; República Checa. University Of Notre Dame-Indiana; Estados Unidos. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Dolensky, Bohumil. Institute of Chemical Technology; República Checa
Fil: Krchnak, Viktor. Palacký University; República Checa. University Of Notre Dame-Indiana; Estados Unidos
Materia
Fused Heterocycles
Iminium
Peptidomimetics
Stereoselectivity
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:11336/21577
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Polymer-Supported Stereoselective Synthesis of Tetrahydro-2H-oxazolo[3,2-a]pyrazin-5(3H)-ones from N-(2-Oxo-ethyl)-Derivatized Dipeptides via Eastbound Iminiumsla Venia, AgustinaDolensky, BohumilKrchnak, ViktorFused HeterocyclesIminiumPeptidomimeticsStereoselectivityhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Polymer-supported N-(2-oxo-ethyl)-derivatized Ser/Thr/Cys-containing dipeptides were synthesized and subjected to acid-mediated tandem N-acylium ion cyclization−nucleophilic addition to yield tetrahydro-2H-oxazolo- [3,2-a]pyrazin-5(3H)-ones. The reaction conditions and building-block combinations for stereoselective synthesis of the newly formed asymmetric carbon were developed. The synthesis was fully compatible with solid-phase peptide synthesis, and the products serve as conformationally constrained peptidomimetics. The traceless synthesis of bicycles is also reported as part of this work.Fil: la Venia, Agustina. Palacký University; República Checa. University Of Notre Dame-Indiana; Estados Unidos. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Dolensky, Bohumil. Institute of Chemical Technology; República ChecaFil: Krchnak, Viktor. Palacký University; República Checa. University Of Notre Dame-Indiana; Estados UnidosAmerican Chemical Society2013-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/21577la Venia, Agustina; Dolensky, Bohumil; Krchnak, Viktor; Polymer-Supported Stereoselective Synthesis of Tetrahydro-2H-oxazolo[3,2-a]pyrazin-5(3H)-ones from N-(2-Oxo-ethyl)-Derivatized Dipeptides via Eastbound Iminiums; American Chemical Society; ACS Combinatorial Science; 15; 3; 2-2013; 162-1672156-8952CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/co3001567info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/co3001567info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:43:59Zoai:ri.conicet.gov.ar:11336/21577instacron: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 10:43:59.33CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Polymer-Supported Stereoselective Synthesis of Tetrahydro-2H-oxazolo[3,2-a]pyrazin-5(3H)-ones from N-(2-Oxo-ethyl)-Derivatized Dipeptides via Eastbound Iminiums
title Polymer-Supported Stereoselective Synthesis of Tetrahydro-2H-oxazolo[3,2-a]pyrazin-5(3H)-ones from N-(2-Oxo-ethyl)-Derivatized Dipeptides via Eastbound Iminiums
spellingShingle Polymer-Supported Stereoselective Synthesis of Tetrahydro-2H-oxazolo[3,2-a]pyrazin-5(3H)-ones from N-(2-Oxo-ethyl)-Derivatized Dipeptides via Eastbound Iminiums
la Venia, Agustina
Fused Heterocycles
Iminium
Peptidomimetics
Stereoselectivity
title_short Polymer-Supported Stereoselective Synthesis of Tetrahydro-2H-oxazolo[3,2-a]pyrazin-5(3H)-ones from N-(2-Oxo-ethyl)-Derivatized Dipeptides via Eastbound Iminiums
title_full Polymer-Supported Stereoselective Synthesis of Tetrahydro-2H-oxazolo[3,2-a]pyrazin-5(3H)-ones from N-(2-Oxo-ethyl)-Derivatized Dipeptides via Eastbound Iminiums
title_fullStr Polymer-Supported Stereoselective Synthesis of Tetrahydro-2H-oxazolo[3,2-a]pyrazin-5(3H)-ones from N-(2-Oxo-ethyl)-Derivatized Dipeptides via Eastbound Iminiums
title_full_unstemmed Polymer-Supported Stereoselective Synthesis of Tetrahydro-2H-oxazolo[3,2-a]pyrazin-5(3H)-ones from N-(2-Oxo-ethyl)-Derivatized Dipeptides via Eastbound Iminiums
title_sort Polymer-Supported Stereoselective Synthesis of Tetrahydro-2H-oxazolo[3,2-a]pyrazin-5(3H)-ones from N-(2-Oxo-ethyl)-Derivatized Dipeptides via Eastbound Iminiums
dc.creator.none.fl_str_mv la Venia, Agustina
Dolensky, Bohumil
Krchnak, Viktor
author la Venia, Agustina
author_facet la Venia, Agustina
Dolensky, Bohumil
Krchnak, Viktor
author_role author
author2 Dolensky, Bohumil
Krchnak, Viktor
author2_role author
author
dc.subject.none.fl_str_mv Fused Heterocycles
Iminium
Peptidomimetics
Stereoselectivity
topic Fused Heterocycles
Iminium
Peptidomimetics
Stereoselectivity
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Polymer-supported N-(2-oxo-ethyl)-derivatized Ser/Thr/Cys-containing dipeptides were synthesized and subjected to acid-mediated tandem N-acylium ion cyclization−nucleophilic addition to yield tetrahydro-2H-oxazolo- [3,2-a]pyrazin-5(3H)-ones. The reaction conditions and building-block combinations for stereoselective synthesis of the newly formed asymmetric carbon were developed. The synthesis was fully compatible with solid-phase peptide synthesis, and the products serve as conformationally constrained peptidomimetics. The traceless synthesis of bicycles is also reported as part of this work.
Fil: la Venia, Agustina. Palacký University; República Checa. University Of Notre Dame-Indiana; Estados Unidos. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Dolensky, Bohumil. Institute of Chemical Technology; República Checa
Fil: Krchnak, Viktor. Palacký University; República Checa. University Of Notre Dame-Indiana; Estados Unidos
description Polymer-supported N-(2-oxo-ethyl)-derivatized Ser/Thr/Cys-containing dipeptides were synthesized and subjected to acid-mediated tandem N-acylium ion cyclization−nucleophilic addition to yield tetrahydro-2H-oxazolo- [3,2-a]pyrazin-5(3H)-ones. The reaction conditions and building-block combinations for stereoselective synthesis of the newly formed asymmetric carbon were developed. The synthesis was fully compatible with solid-phase peptide synthesis, and the products serve as conformationally constrained peptidomimetics. The traceless synthesis of bicycles is also reported as part of this work.
publishDate 2013
dc.date.none.fl_str_mv 2013-02
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/11336/21577
la Venia, Agustina; Dolensky, Bohumil; Krchnak, Viktor; Polymer-Supported Stereoselective Synthesis of Tetrahydro-2H-oxazolo[3,2-a]pyrazin-5(3H)-ones from N-(2-Oxo-ethyl)-Derivatized Dipeptides via Eastbound Iminiums; American Chemical Society; ACS Combinatorial Science; 15; 3; 2-2013; 162-167
2156-8952
CONICET Digital
CONICET
url http://hdl.handle.net/11336/21577
identifier_str_mv la Venia, Agustina; Dolensky, Bohumil; Krchnak, Viktor; Polymer-Supported Stereoselective Synthesis of Tetrahydro-2H-oxazolo[3,2-a]pyrazin-5(3H)-ones from N-(2-Oxo-ethyl)-Derivatized Dipeptides via Eastbound Iminiums; American Chemical Society; ACS Combinatorial Science; 15; 3; 2-2013; 162-167
2156-8952
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/co3001567
info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/co3001567
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
_version_ 1844614476155846656
score 13.070432

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