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https://hdl.handle.net/1822/1347
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Campo DC | Valor | Idioma |
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dc.contributor.author | Lima, Sílvia M. M. A. Pereira | - |
dc.contributor.author | Costa, Susana P. G. | - |
dc.contributor.author | Maia, Hernâni L. S. | - |
dc.date.accessioned | 2005-04-29T15:11:46Z | - |
dc.date.available | 2005-04-29T15:11:46Z | - |
dc.date.issued | 2001 | - |
dc.identifier.citation | 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 | eng |
dc.identifier.uri | https://hdl.handle.net/1822/1347 | - |
dc.description.abstract | 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. | eng |
dc.language.iso | eng | eng |
dc.publisher | Editions EDK | eng |
dc.rights | openAccess | eng |
dc.subject | Amide bond | eng |
dc.subject | C,alfa,alfa-disubstituted glycines | eng |
dc.subject | Stabylity | eng |
dc.subject | Ugi-Passerini Reaction | eng |
dc.title | C-terminal amide bond stability of peptides containing C,alfa,alfa-disubstituted glycines | eng |
dc.type | conferenceAbstract | eng |
dc.peerreviewed | yes | eng |
Aparece nas coleções: | CDQuim - Comunicações e Proceedings |
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article.pdf | 32,23 kB | Adobe PDF | Ver/Abrir |