C-terminal amide bond stability of peptides containing C,alfa,alfa-disubstituted glycines

Detalhes bibliográficos
Autor(a) principal: Lima, Sílvia M. M. A. Pereira
Data de Publicação: 2001
Outros Autores: Costa, Susana P. G., Maia, Hernâni L. S.
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/1822/1347
Resumo: We have since long been interested in the synthesis of C,alfa,alfa-disubstituted glycines using the Ugi Four Component Condensation Reaction. Recently we have improved this method of synthesis by using 4-methoxybenzyl amine as the amine component of the Ugi reaction (A), which allowed an important simplification in the subsequent cleavage of the product. During the removal of the 4-methoxybenzyl group with hot neat TFA, we detected that not only this group was removed but also the C-terminal amide bond was cleaved. This result was independent of the nature of the amino acid residue so far generated and of the N-substituent at the C-terminal amide group. After work-up in aqueous media, the N-acetyl amino acids were isolated in quantitative yield. A similar behaviour was reported by Goodman et al., but with dimethylglycine derivatives having a methyl group at the nitrogen atom of this residue. In our case cleavage appears to occur even after removal of the N-alkyl group. These results prompted us to a further thorough study of the stability of this peptide bond under different conditions, by changing the acid used and the temperature of the reaction mixture.
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spelling C-terminal amide bond stability of peptides containing C,alfa,alfa-disubstituted glycinesAmide bondC,alfa,alfa-disubstituted glycinesStabylityUgi-Passerini ReactionWe have since long been interested in the synthesis of C,alfa,alfa-disubstituted glycines using the Ugi Four Component Condensation Reaction. Recently we have improved this method of synthesis by using 4-methoxybenzyl amine as the amine component of the Ugi reaction (A), which allowed an important simplification in the subsequent cleavage of the product. During the removal of the 4-methoxybenzyl group with hot neat TFA, we detected that not only this group was removed but also the C-terminal amide bond was cleaved. This result was independent of the nature of the amino acid residue so far generated and of the N-substituent at the C-terminal amide group. After work-up in aqueous media, the N-acetyl amino acids were isolated in quantitative yield. A similar behaviour was reported by Goodman et al., but with dimethylglycine derivatives having a methyl group at the nitrogen atom of this residue. In our case cleavage appears to occur even after removal of the N-alkyl group. These results prompted us to a further thorough study of the stability of this peptide bond under different conditions, by changing the acid used and the temperature of the reaction mixture.Editions EDKUniversidade do MinhoLima, Sílvia M. M. A. PereiraCosta, Susana P. G.Maia, Hernâni L. S.20012001-01-01T00:00:00Zconference objectinfo:eu-repo/semantics/publishedVersionapplication/pdfhttp://hdl.handle.net/1822/1347engFEHRENTZ, Jean-Alian, ed. lit. - “Peptides 2000 : proceedings of the twenty-sixth Eropean Peptide Simposium, 26, Montpellier, 2000”. Paris : EDK, 2001. ISBN 2-8425-4048-4. p.367-368info: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:RCAAP2024-05-11T06:30:47Zoai:repositorium.sdum.uminho.pt:1822/1347Portal AgregadorONGhttps://www.rcaap.pt/oai/openairemluisa.alvim@gmail.comopendoar:71602024-05-11T06:30:47Repositório 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 C-terminal amide bond stability of peptides containing C,alfa,alfa-disubstituted glycines
title C-terminal amide bond stability of peptides containing C,alfa,alfa-disubstituted glycines
spellingShingle C-terminal amide bond stability of peptides containing C,alfa,alfa-disubstituted glycines
Lima, Sílvia M. M. A. Pereira
Amide bond
C,alfa,alfa-disubstituted glycines
Stabylity
Ugi-Passerini Reaction
title_short C-terminal amide bond stability of peptides containing C,alfa,alfa-disubstituted glycines
title_full C-terminal amide bond stability of peptides containing C,alfa,alfa-disubstituted glycines
title_fullStr C-terminal amide bond stability of peptides containing C,alfa,alfa-disubstituted glycines
title_full_unstemmed C-terminal amide bond stability of peptides containing C,alfa,alfa-disubstituted glycines
title_sort C-terminal amide bond stability of peptides containing C,alfa,alfa-disubstituted glycines
author Lima, Sílvia M. M. A. Pereira
author_facet Lima, Sílvia M. M. A. Pereira
Costa, Susana P. G.
Maia, Hernâni L. S.
author_role author
author2 Costa, Susana P. G.
Maia, Hernâni L. S.
author2_role author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Lima, Sílvia M. M. A. Pereira
Costa, Susana P. G.
Maia, Hernâni L. S.
dc.subject.por.fl_str_mv Amide bond
C,alfa,alfa-disubstituted glycines
Stabylity
Ugi-Passerini Reaction
topic Amide bond
C,alfa,alfa-disubstituted glycines
Stabylity
Ugi-Passerini Reaction
description We have since long been interested in the synthesis of C,alfa,alfa-disubstituted glycines using the Ugi Four Component Condensation Reaction. Recently we have improved this method of synthesis by using 4-methoxybenzyl amine as the amine component of the Ugi reaction (A), which allowed an important simplification in the subsequent cleavage of the product. During the removal of the 4-methoxybenzyl group with hot neat TFA, we detected that not only this group was removed but also the C-terminal amide bond was cleaved. This result was independent of the nature of the amino acid residue so far generated and of the N-substituent at the C-terminal amide group. After work-up in aqueous media, the N-acetyl amino acids were isolated in quantitative yield. A similar behaviour was reported by Goodman et al., but with dimethylglycine derivatives having a methyl group at the nitrogen atom of this residue. In our case cleavage appears to occur even after removal of the N-alkyl group. These results prompted us to a further thorough study of the stability of this peptide bond under different conditions, by changing the acid used and the temperature of the reaction mixture.
publishDate 2001
dc.date.none.fl_str_mv 2001
2001-01-01T00:00:00Z
dc.type.driver.fl_str_mv conference object
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/1822/1347
url http://hdl.handle.net/1822/1347
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv FEHRENTZ, Jean-Alian, ed. lit. - “Peptides 2000 : proceedings of the twenty-sixth Eropean Peptide Simposium, 26, Montpellier, 2000”. Paris : EDK, 2001. ISBN 2-8425-4048-4. p.367-368
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 Editions EDK
publisher.none.fl_str_mv Editions EDK
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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