C-terminal amide bond stability of peptides containing C,alfa,alfa-disubstituted glycines
Autor(a) principal: | |
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Data de Publicação: | 2001 |
Outros Autores: | , |
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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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 |
_version_ |
1817544997963038720 |