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https://hdl.handle.net/1822/15962
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Campo DC | Valor | Idioma |
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dc.contributor.author | Monteiro, Luís S. | - |
dc.contributor.author | Andrade, Juliana J. | - |
dc.contributor.author | Suárez, Ana C. | - |
dc.date.accessioned | 2011-12-28T14:15:27Z | - |
dc.date.available | 2011-12-28T14:15:27Z | - |
dc.date.issued | 2011-11 | - |
dc.identifier.issn | 1434-193X | por |
dc.identifier.uri | https://hdl.handle.net/1822/15962 | - |
dc.description.abstract | Recently we reported the use of a sequence of alkylation and dehydration methodologies to obtain from the methyl esters of N-(4-nitrophenylsulfonyl)-β-hydroxyamino acids, new non-proteinogenic amino acids, namely, N-ethyl-α,β-dehydroamino acids. Thus, it was possible to obtain for the first time, non-natural amino acids which incorporate both the N-ethyl and α,β-dehydro moieties. Herein, we report 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 such as tert-butyloxycarbonyl, benzyloxycarbonyl and 4-nitrobenzyloxycarbonyl as well as acyl and sulfonyl groups. The procedure allows the synthesis of the methyl esters of N-protected, N-ethyl, β,β-dibromo and N-ethyl, β-bromo, β-substituted dehydroamino acids in fair to high yields. Some of these N-ethylated dehydroamino acid derivatives were used as substrates in cross coupling reactions to give N-ethyl, β,β-disubstituted dehydroalanine derivatives. | por |
dc.description.sponsorship | The Portuguese Foundation for Science and Technology (FCT) and the Fundo Europeu de Desenvolvimento Regional (FEDER) are thanked for financial support to the Chemistry Centre of University of Minho. The Bruker Avance II<SUP>+</SUP> 400 NMR spectrometer is part of the National NMR Network and was purchased in the framework of the National Program for Scientific Re-equipment, REDE/1517/RMN/2005, with funds from POCI 2010, FEDER and FCT. | por |
dc.language.iso | eng | por |
dc.publisher | Wiley-VCH Verlag | por |
dc.rights | openAccess | por |
dc.subject | Amino acids | por |
dc.subject | Alkylation | por |
dc.subject | N-Ethyl dehydroamino acids | por |
dc.subject | N-Ethyl β-bromo dehydroamino acids | por |
dc.subject | Suzuki cross-coupling | por |
dc.subject | Nonnatural amino acids | por |
dc.subject | Cross-coupling | por |
dc.subject | Protecting groups | por |
dc.title | Synthesis of new n-ethyl dehydroamino acid derivatives : n-ethyl β,β-dibromo, n-ethyl β-bromo β-substituted, n-ethyl β,β-disubstituted n-protected dehydroamino acid methyl esters | por |
dc.type | article | por |
dc.peerreviewed | yes | por |
sdum.publicationstatus | published | por |
oaire.citationStartPage | 6764 | por |
oaire.citationEndPage | 6772 | por |
oaire.citationIssue | 33 | por |
oaire.citationTitle | European Journal of Organic Chemistry | por |
oaire.citationVolume | 33 | por |
dc.identifier.doi | 10.1002/ejoc.201100907 | - |
dc.subject.wos | Science & Technology | por |
sdum.journal | European Journal of Organic Chemistry | por |
Aparece nas coleções: | CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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2011-Eur. J. Org. Chem I.pdf | 259,56 kB | Adobe PDF | Ver/Abrir |