Synthesis and conformational investigation of tetrapeptide analogues of the fragment B23-B26 of insulin

Detalhes bibliográficos
Autor(a) principal: Rodrigues, Lígia M.
Data de Publicação: 2004
Outros Autores: Fonseca, José I., Maia, Hernâni L. S.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: https://hdl.handle.net/1822/1026
Resumo: Tetrapeptides containing one of a set of four different alpha,alpha-dialkyl glycines at the C-terminus were synthesized by conventional methods in solution and their conformational behavior investigated by 1H NMR spectroscopy in connection with molecular mechanics calculations. The results were consistent with conformations stabilized by a gama-turn in the case of compounds with alkyl groups larger than methyl, while the corresponding Aib derivative did not exhibit intramolecular hydrogen bonding.
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spelling Synthesis and conformational investigation of tetrapeptide analogues of the fragment B23-B26 of insulinPeptide synthesisConformational analysisNMRAlphaAlpha-dialkyl glycinesalpha,alpha-dialkyl glycinesScience & TechnologyTetrapeptides containing one of a set of four different alpha,alpha-dialkyl glycines at the C-terminus were synthesized by conventional methods in solution and their conformational behavior investigated by 1H NMR spectroscopy in connection with molecular mechanics calculations. The results were consistent with conformations stabilized by a gama-turn in the case of compounds with alkyl groups larger than methyl, while the corresponding Aib derivative did not exhibit intramolecular hydrogen bonding.Foram sintetisados tetrapéptidos contendo um duma série de quatro aminoácidos alfa-alfa disubstituídos, por métodos convencionais. As preferências conformacionais foram deduzidas por RMN de protão e por calculo de modelação molecular. Os resultados são consistentes com conformações estabilizadas por dobras gama nos casos dos compostos com grupos alquilo maiores que o metilo, enquanto que o derivado com Aib não mostra qualquer ligação de hidrogénio intramolecular.Elsevier 1Universidade do MinhoRodrigues, Lígia M.Fonseca, José I.Maia, Hernâni L. S.20042004-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/1822/1026eng"Tetrahedron". 60 (2004) 8929-8936.0040-402010.1016/j.tet.2004.07.014info: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:RCAAP2024-05-25T01:53:19Zoai:repositorium.sdum.uminho.pt:1822/1026Portal AgregadorONGhttps://www.rcaap.pt/oai/openairemluisa.alvim@gmail.comopendoar:71602024-05-25T01:53:19Repositório 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 Synthesis and conformational investigation of tetrapeptide analogues of the fragment B23-B26 of insulin
title Synthesis and conformational investigation of tetrapeptide analogues of the fragment B23-B26 of insulin
spellingShingle Synthesis and conformational investigation of tetrapeptide analogues of the fragment B23-B26 of insulin
Rodrigues, Lígia M.
Peptide synthesis
Conformational analysis
NMR
Alpha
Alpha-dialkyl glycines
alpha,alpha-dialkyl glycines
Science & Technology
title_short Synthesis and conformational investigation of tetrapeptide analogues of the fragment B23-B26 of insulin
title_full Synthesis and conformational investigation of tetrapeptide analogues of the fragment B23-B26 of insulin
title_fullStr Synthesis and conformational investigation of tetrapeptide analogues of the fragment B23-B26 of insulin
title_full_unstemmed Synthesis and conformational investigation of tetrapeptide analogues of the fragment B23-B26 of insulin
title_sort Synthesis and conformational investigation of tetrapeptide analogues of the fragment B23-B26 of insulin
author Rodrigues, Lígia M.
author_facet Rodrigues, Lígia M.
Fonseca, José I.
Maia, Hernâni L. S.
author_role author
author2 Fonseca, José I.
Maia, Hernâni L. S.
author2_role author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Rodrigues, Lígia M.
Fonseca, José I.
Maia, Hernâni L. S.
dc.subject.por.fl_str_mv Peptide synthesis
Conformational analysis
NMR
Alpha
Alpha-dialkyl glycines
alpha,alpha-dialkyl glycines
Science & Technology
topic Peptide synthesis
Conformational analysis
NMR
Alpha
Alpha-dialkyl glycines
alpha,alpha-dialkyl glycines
Science & Technology
description Tetrapeptides containing one of a set of four different alpha,alpha-dialkyl glycines at the C-terminus were synthesized by conventional methods in solution and their conformational behavior investigated by 1H NMR spectroscopy in connection with molecular mechanics calculations. The results were consistent with conformations stabilized by a gama-turn in the case of compounds with alkyl groups larger than methyl, while the corresponding Aib derivative did not exhibit intramolecular hydrogen bonding.
publishDate 2004
dc.date.none.fl_str_mv 2004
2004-01-01T00:00:00Z
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 https://hdl.handle.net/1822/1026
url https://hdl.handle.net/1822/1026
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv "Tetrahedron". 60 (2004) 8929-8936.
0040-4020
10.1016/j.tet.2004.07.014
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 Elsevier 1
publisher.none.fl_str_mv Elsevier 1
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
instname_str 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)
collection 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 mluisa.alvim@gmail.com
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