Convergent Approaches for the Synthesis of the Anti-tumoral Peptide, Kahalalide F. Study of Orthogonal Protecting Groups

Kahalalide compounds are peptides that are isolated from a Hawaiian herbivorous marine species of mollusc, Elysia rufescens, and its diet, the green alga Bryopsis sp. Kahalalide F and its synthetic analogues are the most promising compounds of the Kahalalide family because they show anti-tumoral act...

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Autores: Gracia, Carolina, Isidro Llobet, Albert, Cruz, Luis J., Acosta, Gerardo A., Álvarez Domingo, Mercedes, Cuevas, Carmen, Giralt Lledó, Ernest, Albericio Palomera, Fernando
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2006
País:España
Institución:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/48635
Acceso en línea:https://hdl.handle.net/2445/48635
Access Level:acceso abierto
Palabra clave:Pèptids
Medicaments antineoplàstics
Productes naturals marins
Peptides
Antineoplastic agents
Marine natural products
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spelling Convergent Approaches for the Synthesis of the Anti-tumoral Peptide, Kahalalide F. Study of Orthogonal Protecting GroupsGracia, CarolinaIsidro Llobet, AlbertCruz, Luis J.Acosta, Gerardo A.Álvarez Domingo, MercedesCuevas, CarmenGiralt Lledó, ErnestAlbericio Palomera, FernandoPèptidsMedicaments antineoplàsticsProductes naturals marinsPeptidesAntineoplastic agentsMarine natural productsKahalalide compounds are peptides that are isolated from a Hawaiian herbivorous marine species of mollusc, Elysia rufescens, and its diet, the green alga Bryopsis sp. Kahalalide F and its synthetic analogues are the most promising compounds of the Kahalalide family because they show anti-tumoral activity. Linear solid-phase syntheses of Kahalalide F have been reported. Here we describe several new improved synthetic routes based on convergent approaches with distinct orthogonal protection schemes for the preparation of Kahaladide analogues. These strategies allow a better control and characterization of the intermediates because more reactions are performed in solution. Five derivatives of Kahalalide F were synthesized using several convergent approaches.American Chemical Society2006info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttps://hdl.handle.net/2445/48635Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)reponame:Dipòsit Digital de la UBinstname:Universidad de BarcelonaInglésJournal of Organic Chemistry, 2006, vol. 71, p. 7196(c) American Chemical Society , 2006info:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/486352026-05-27T06:46:51Z
dc.title.none.fl_str_mv Convergent Approaches for the Synthesis of the Anti-tumoral Peptide, Kahalalide F. Study of Orthogonal Protecting Groups
title Convergent Approaches for the Synthesis of the Anti-tumoral Peptide, Kahalalide F. Study of Orthogonal Protecting Groups
spellingShingle Convergent Approaches for the Synthesis of the Anti-tumoral Peptide, Kahalalide F. Study of Orthogonal Protecting Groups
Gracia, Carolina
Pèptids
Medicaments antineoplàstics
Productes naturals marins
Peptides
Antineoplastic agents
Marine natural products
title_short Convergent Approaches for the Synthesis of the Anti-tumoral Peptide, Kahalalide F. Study of Orthogonal Protecting Groups
title_full Convergent Approaches for the Synthesis of the Anti-tumoral Peptide, Kahalalide F. Study of Orthogonal Protecting Groups
title_fullStr Convergent Approaches for the Synthesis of the Anti-tumoral Peptide, Kahalalide F. Study of Orthogonal Protecting Groups
title_full_unstemmed Convergent Approaches for the Synthesis of the Anti-tumoral Peptide, Kahalalide F. Study of Orthogonal Protecting Groups
title_sort Convergent Approaches for the Synthesis of the Anti-tumoral Peptide, Kahalalide F. Study of Orthogonal Protecting Groups
dc.creator.none.fl_str_mv Gracia, Carolina
Isidro Llobet, Albert
Cruz, Luis J.
Acosta, Gerardo A.
Álvarez Domingo, Mercedes
Cuevas, Carmen
Giralt Lledó, Ernest
Albericio Palomera, Fernando
author Gracia, Carolina
author_facet Gracia, Carolina
Isidro Llobet, Albert
Cruz, Luis J.
Acosta, Gerardo A.
Álvarez Domingo, Mercedes
Cuevas, Carmen
Giralt Lledó, Ernest
Albericio Palomera, Fernando
author_role author
author2 Isidro Llobet, Albert
Cruz, Luis J.
Acosta, Gerardo A.
Álvarez Domingo, Mercedes
Cuevas, Carmen
Giralt Lledó, Ernest
Albericio Palomera, Fernando
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Pèptids
Medicaments antineoplàstics
Productes naturals marins
Peptides
Antineoplastic agents
Marine natural products
topic Pèptids
Medicaments antineoplàstics
Productes naturals marins
Peptides
Antineoplastic agents
Marine natural products
description Kahalalide compounds are peptides that are isolated from a Hawaiian herbivorous marine species of mollusc, Elysia rufescens, and its diet, the green alga Bryopsis sp. Kahalalide F and its synthetic analogues are the most promising compounds of the Kahalalide family because they show anti-tumoral activity. Linear solid-phase syntheses of Kahalalide F have been reported. Here we describe several new improved synthetic routes based on convergent approaches with distinct orthogonal protection schemes for the preparation of Kahaladide analogues. These strategies allow a better control and characterization of the intermediates because more reactions are performed in solution. Five derivatives of Kahalalide F were synthesized using several convergent approaches.
publishDate 2006
dc.date.none.fl_str_mv 2006
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/2445/48635
url https://hdl.handle.net/2445/48635
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Journal of Organic Chemistry, 2006, vol. 71, p. 7196
dc.rights.none.fl_str_mv (c) American Chemical Society , 2006
info:eu-repo/semantics/openAccess
rights_invalid_str_mv (c) American Chemical Society , 2006
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 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 (Farmacologia, Toxicologia i Química Terapèutica)
reponame:Dipòsit Digital de la UB
instname:Universidad de Barcelona
instname_str Universidad de Barcelona
reponame_str Dipòsit Digital de la UB
collection Dipòsit Digital de la UB
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,300719

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