Photorelease of amino acids from novel thioxobenzo[f]benzopyran ester conjugates
Autor(a) principal: | |
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Data de Publicação: | 2012 |
Outros Autores: | , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/1822/13095 |
Resumo: | Aiming at the enhancement of the performance of (9-methoxy-3-oxo-3H-benzo[f]benzopyran-1-yl) methyl ester as photocleavable protecting group for the carboxylic acid function at long-wavelengths, 9-methoxy-3-thioxo-3H-benzo[f]benzopyran-L-valine and L-phenylalanine model conjugates were prepared through a thionation reaction of the corresponding oxo-benzobenzopyrans. These thioxobenzobenzopyran derivatives were subjected to photocleavage reactions in the same conditions as the parent oxo-benzobenzopyrans at different wavelengths of irradiation, and photocleavage kinetic data was obtained. It was found that the exchange of the carbonyl by a thiocarbonyl group enhanced the performance of the heterocyclic protecting group at 419 nm by improving the photolysis rates, making it an appropriate group for practical applications at long wavelengths. |
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Photorelease of amino acids from novel thioxobenzo[f]benzopyran ester conjugatesThioxobenzobenzopyranBenzocoumarinAmino acidsPhotolabile protecting groupsScience & TechnologyAiming at the enhancement of the performance of (9-methoxy-3-oxo-3H-benzo[f]benzopyran-1-yl) methyl ester as photocleavable protecting group for the carboxylic acid function at long-wavelengths, 9-methoxy-3-thioxo-3H-benzo[f]benzopyran-L-valine and L-phenylalanine model conjugates were prepared through a thionation reaction of the corresponding oxo-benzobenzopyrans. These thioxobenzobenzopyran derivatives were subjected to photocleavage reactions in the same conditions as the parent oxo-benzobenzopyrans at different wavelengths of irradiation, and photocleavage kinetic data was obtained. It was found that the exchange of the carbonyl by a thiocarbonyl group enhanced the performance of the heterocyclic protecting group at 419 nm by improving the photolysis rates, making it an appropriate group for practical applications at long wavelengths.Fundo Europeu de Desenvolvimento Regional (FEDER) - POCI 2010Fundação para a Ciência e a Tecnologia (FCT) - REDE/1517/RMN/2005Springer VerlagUniversidade do MinhoPiloto, Ana M.Soares, Ana M. S.Costa, Susana P. G.Gonçalves, M. Sameiro T.20122012-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/13095eng0939-445110.1007/s00726-011-0969-021739147http://www.springerlink.com/info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-07-21T12:09:17Zoai:repositorium.sdum.uminho.pt:1822/13095Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:00:40.379319Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
Photorelease of amino acids from novel thioxobenzo[f]benzopyran ester conjugates |
title |
Photorelease of amino acids from novel thioxobenzo[f]benzopyran ester conjugates |
spellingShingle |
Photorelease of amino acids from novel thioxobenzo[f]benzopyran ester conjugates Piloto, Ana M. Thioxobenzobenzopyran Benzocoumarin Amino acids Photolabile protecting groups Science & Technology |
title_short |
Photorelease of amino acids from novel thioxobenzo[f]benzopyran ester conjugates |
title_full |
Photorelease of amino acids from novel thioxobenzo[f]benzopyran ester conjugates |
title_fullStr |
Photorelease of amino acids from novel thioxobenzo[f]benzopyran ester conjugates |
title_full_unstemmed |
Photorelease of amino acids from novel thioxobenzo[f]benzopyran ester conjugates |
title_sort |
Photorelease of amino acids from novel thioxobenzo[f]benzopyran ester conjugates |
author |
Piloto, Ana M. |
author_facet |
Piloto, Ana M. Soares, Ana M. S. Costa, Susana P. G. Gonçalves, M. Sameiro T. |
author_role |
author |
author2 |
Soares, Ana M. S. Costa, Susana P. G. Gonçalves, M. Sameiro T. |
author2_role |
author author author |
dc.contributor.none.fl_str_mv |
Universidade do Minho |
dc.contributor.author.fl_str_mv |
Piloto, Ana M. Soares, Ana M. S. Costa, Susana P. G. Gonçalves, M. Sameiro T. |
dc.subject.por.fl_str_mv |
Thioxobenzobenzopyran Benzocoumarin Amino acids Photolabile protecting groups Science & Technology |
topic |
Thioxobenzobenzopyran Benzocoumarin Amino acids Photolabile protecting groups Science & Technology |
description |
Aiming at the enhancement of the performance of (9-methoxy-3-oxo-3H-benzo[f]benzopyran-1-yl) methyl ester as photocleavable protecting group for the carboxylic acid function at long-wavelengths, 9-methoxy-3-thioxo-3H-benzo[f]benzopyran-L-valine and L-phenylalanine model conjugates were prepared through a thionation reaction of the corresponding oxo-benzobenzopyrans. These thioxobenzobenzopyran derivatives were subjected to photocleavage reactions in the same conditions as the parent oxo-benzobenzopyrans at different wavelengths of irradiation, and photocleavage kinetic data was obtained. It was found that the exchange of the carbonyl by a thiocarbonyl group enhanced the performance of the heterocyclic protecting group at 419 nm by improving the photolysis rates, making it an appropriate group for practical applications at long wavelengths. |
publishDate |
2012 |
dc.date.none.fl_str_mv |
2012 2012-01-01T00:00:00Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/1822/13095 |
url |
http://hdl.handle.net/1822/13095 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
0939-4451 10.1007/s00726-011-0969-0 21739147 http://www.springerlink.com/ |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Springer Verlag |
publisher.none.fl_str_mv |
Springer Verlag |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
instacron_str |
RCAAP |
institution |
RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
repository.name.fl_str_mv |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
repository.mail.fl_str_mv |
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1799132403022692352 |