Publicação
Photorelease of amino acids from novel thioxobenzo[f]benzopyran ester conjugates
| 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. |
|---|---|
| Autores principais: | Piloto, Ana M. |
| Outros Autores: | Soares, Ana M. S.; Costa, Susana P. G.; Gonçalves, M. Sameiro T. |
| Assunto: | Thioxobenzobenzopyran Benzocoumarin Amino acids Photolabile protecting groups |
| Ano: | 2012 |
| País: | Portugal |
| Tipo de documento: | artigo |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | Universidade do Minho |
| Idioma: | inglês |
| Origem: | RepositóriUM - Universidade do Minho |
| _version_ | 1867438336131465216 |
|---|---|
| author | Piloto, Ana M. |
| author2 | Soares, Ana M. S. Costa, Susana P. G. Gonçalves, M. Sameiro T. |
| author2_role | author author author |
| author_facet | Piloto, Ana M. Soares, Ana M. S. Costa, Susana P. G. Gonçalves, M. Sameiro T. |
| author_role | author |
| contributor_name_str_mv | RepositóriUM - Universidade do Minho |
| country_str | PT |
| creators_json_txt | [{\"Person.name\":\"Piloto, Ana M.\"},{\"Person.name\":\"Soares, Ana M. S.\"},{\"Person.name\":\"Costa, Susana P. G.\"},{\"Person.name\":\"Gonçalves, M. Sameiro T.\"}] |
| datacite.contributors.contributor.contributorName.fl_str_mv | RepositóriUM - Universidade do Minho |
| datacite.creators.creator.creatorName.fl_str_mv | Piloto, Ana M. Soares, Ana M. S. Costa, Susana P. G. Gonçalves, M. Sameiro T. |
| datacite.date.Accepted.fl_str_mv | 2012-01-01T00:00:00Z |
| datacite.date.available.fl_str_mv | 2011-07-27T10:28:35Z |
| datacite.date.embargoed.fl_str_mv | 2011-07-27T10:28:35Z |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| datacite.subjects.subject.fl_str_mv | Thioxobenzobenzopyran Benzocoumarin Amino acids Photolabile protecting groups |
| datacite.titles.title.fl_str_mv | Photorelease of amino acids from novel thioxobenzo[f]benzopyran ester conjugates |
| dc.contributor.none.fl_str_mv | RepositóriUM - Universidade do Minho |
| dc.creator.none.fl_str_mv | Piloto, Ana M. Soares, Ana M. S. Costa, Susana P. G. Gonçalves, M. Sameiro T. |
| dc.date.Accepted.fl_str_mv | 2012-01-01T00:00:00Z |
| dc.date.available.fl_str_mv | 2011-07-27T10:28:35Z |
| dc.date.embargoed.fl_str_mv | 2011-07-27T10:28:35Z |
| dc.format.none.fl_str_mv | application/pdf |
| dc.identifier.none.fl_str_mv | https://hdl.handle.net/1822/13095 |
| dc.language.none.fl_str_mv | eng |
| dc.publisher.none.fl_str_mv | Springer Verlag |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| dc.subject.none.fl_str_mv | Thioxobenzobenzopyran Benzocoumarin Amino acids Photolabile protecting groups |
| dc.title.fl_str_mv | Photorelease of amino acids from novel thioxobenzo[f]benzopyran ester conjugates |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_6501 |
| 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. |
| dirty | 0 |
| eu_rights_str_mv | openAccess |
| format | article |
| fulltext.url.fl_str_mv | https://repositorium.uminho.pt/bitstreams/ccbbf19c-4b6f-49dd-a065-094d0b68e869/download |
| id | rum_2cfd2e08ccfe36ccc3cfe32e963d0e9d |
| identifier.url.fl_str_mv | https://hdl.handle.net/1822/13095 |
| instacron_str | repositorium |
| institution | Universidade do Minho |
| instname_str | Universidade do Minho |
| language | eng |
| network_acronym_str | rum |
| network_name_str | RepositóriUM - Universidade do Minho |
| oai_identifier_str | oai:repositorium.uminho.pt:1822/13095 |
| organization_str_mv | urn:organizationAcronym:repositorium |
| person_str_mv | Piloto, Ana M. Soares, Ana M. S. Costa, Susana P. G. Gonçalves, M. Sameiro T. |
| publishDate | 2012 |
| publisher.none.fl_str_mv | Springer Verlag |
| reponame_str | RepositóriUM - Universidade do Minho |
| repository_id_str | urn:repositoryAcronym:rum |
| service_str_mv | urn:repositoryAcronym:rum |
| spelling | engSpringer VerlagporAiming 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.application/pdfporPhotorelease of amino acids from novel thioxobenzo[f]benzopyran ester conjugatesPiloto, Ana M.Soares, Ana M. S.Costa, Susana P. G.Gonçalves, M. Sameiro T.HostingInstitutionOrganizationalRepositóriUM - Universidade do Minhoe-mailmailto:repositorium@usdb.uminho.ptrepositorium@usdb.uminho.ptPMID21739147ISSNIsPartOf0939-4451ISSNIsPartOf1438-2199DOIIsPartOf10.1007/s00726-011-0969-02011-07-27T10:28:35Z20122011-01-202012-01-01T00:00:00ZHandlehttps://hdl.handle.net/1822/13095http://purl.org/coar/access_right/c_abf2open accessThioxobenzobenzopyranBenzocoumarinAmino acidsPhotolabile protecting groups562220 bytesliteraturehttp://purl.org/coar/resource_type/c_6501journal articlehttp://purl.org/coar/access_right/c_abf2application/pdffulltexthttps://repositorium.uminho.pt/bitstreams/ccbbf19c-4b6f-49dd-a065-094d0b68e869/download |
| spellingShingle | Photorelease of amino acids from novel thioxobenzo[f]benzopyran ester conjugates Piloto, Ana M. Thioxobenzobenzopyran Benzocoumarin Amino acids Photolabile protecting groups |
| status | SINGLETON |
| subject.fl_str_mv | Thioxobenzobenzopyran Benzocoumarin Amino acids Photolabile protecting groups |
| title | 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_short | Photorelease of amino acids from novel thioxobenzo[f]benzopyran ester conjugates |
| title_sort | Photorelease of amino acids from novel thioxobenzo[f]benzopyran ester conjugates |
| topic | Thioxobenzobenzopyran Benzocoumarin Amino acids Photolabile protecting groups |
| topic_facet | Thioxobenzobenzopyran Benzocoumarin Amino acids Photolabile protecting groups |
| url | https://hdl.handle.net/1822/13095 |
| visible | 1 |