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https://hdl.handle.net/1822/22065
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Campo DC | Valor | Idioma |
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dc.contributor.author | Monteiro, Luís S. | - |
dc.contributor.author | Suárez, Ana C. | - |
dc.date.accessioned | 2012-12-21T18:54:20Z | - |
dc.date.available | 2012-12-21T18:54:20Z | - |
dc.date.issued | 2012 | - |
dc.identifier.issn | 0939-4451 | por |
dc.identifier.uri | https://hdl.handle.net/1822/22065 | - |
dc.description.abstract | Recently we reported the use of a sequence of alkylation and dehydration methodologies to obtain N-ethyl-α, β-dehydroamino acid derivatives. The application of this N-alkylation procedure to several methyl esters of β, β-dibromo and β--bromo, β-substituted dehydroamino acids protected with standard amine protecting groups was subsequently reported. The corresponding N-ethyl, β-bromo dehydroamino acid derivatives were obtained in fair to high yields and some were used as substrates in Suzuki cross coupling reactions to give N-ethyl, β, β-disubstituted dehydroalanine derivatives. Herein, we further explore N-ethylation of β-halo dehydroamino acid derivatives using triethyloxonium tetrafluoroborate as alkylating agent but substituting N,N-diisopropylethylamine for potassium tert-butoxide as auxiliary base. In these conditions, for all β-halo dehydroamino acid derivatives, reactions were complete and the N-ethylated derivative could be isolated in high yield. This method was also applied for N-ethylation of non-halogenated dehydroamino acids. Again, with all compounds the reactions were complete and the N-ethyl dehydroamino acid derivatives could be isolated in high yields. Some of these N-ethyl dehydroamino acid methyl ester derivatives were converted in high yields to their corresponding acids and coupled to an amino acid methyl ester to give N-ethyl dehydrodipeptide derivatives in good yields. Thus, this method constitutes a general procedure for high yielding synthesis of N-ethylated dehydroamino acids, which can be further applied in peptide synthesis. | por |
dc.description.sponsorship | Foundation for Science and Technology (FCT)-Portugal and Fundo Europeu de Desenvolvimento Regional (FEDER) for financial support to Chemistry Centre of University of Minho. The NMR spectrometer Bruker Avance II<SUP>+</SUP> 400 is part of the National NMR Network and was purchased in the framework of the National Program for Scientific Re-equipment; contract REDE/1517/RMN/2005, with funds from POCI 2010, FEDER and FCT. | por |
dc.language.iso | eng | por |
dc.publisher | Springer | por |
dc.rights | openAccess | por |
dc.subject | Amino acids | por |
dc.subject | Nonnatural amino acids | por |
dc.subject | Alkylation | por |
dc.subject | N-Ethyl dehydroamino acids | por |
dc.subject | Protecting groups | por |
dc.title | High yielding synthesis of N-ethyl dehydroamino acids | por |
dc.type | article | por |
dc.peerreviewed | yes | por |
sdum.publicationstatus | published | por |
oaire.citationStartPage | 1643 | por |
oaire.citationEndPage | 1652 | por |
oaire.citationIssue | 4 | por |
oaire.citationTitle | Amino Acids | por |
oaire.citationVolume | 43 | por |
dc.identifier.doi | 10.1007/s00726-012-1240-z | por |
dc.identifier.pmid | 22349761 | por |
dc.subject.wos | Science & Technology | por |
sdum.journal | Amino Acids | por |
Aparece nas coleções: | CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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2012-Amino Acids I.pdf | 284,95 kB | Adobe PDF | Ver/Abrir |