Utilize este identificador para referenciar este registo: http://hdl.handle.net/1822/48100

TítuloSynthesis of Dehydrodipeptide and N-ethyl-dehydrodipeptide Derivatives with an α-Aminoisobutyric Acid Residue
Autor(es)Monteiro, Luís S.
Pereira-Lima, Sílvia M. M. A.
Pereira, Sofia
Palavras-chaveAlkylation
dehydration
dehydroamino acids
dehydrodipeptide
α, α-Dialkylglicines
N-Alkyl-dehydrodipeptides
N-Alkylamino acids
Data10-Jan-2015
EditoraBentham Science Publishers
RevistaCurrent Chemical Biology
Resumo(s)Several dipeptides with an N-benzyloxycarbonyl or an N-(tert-butyloxycarbonyl) α-aminoisobutyric acid residue and a β-hydroxyamino acid methyl ester were subjected to dehydration to form dehydrodipeptide derivatives. N-Ethylation of these dipeptides using triethyloxonium tetrafluoroborate with potassium tert-butoxide as auxiliary base led to complex mixtures that failed to render pure products. However, when the 4-nitrophenylsulfonyl protecting group was substituted for the benzyloxycarbonyl or tert-butyloxycarbonyl groups and N,N-diisopropylethylamine was substituted for potassium tert-butoxide, the dehydrodipeptide derivatives were selectively N-alkylated at the amino terminal nitrogen in fair to high yields. Alternatively, N-ethylation can be carried out prior to dehydration. Thus, through a combination of dehydration and N-ethylation procedures, it was possible to obtain dipeptides with α-aminoisobutyric acid and dehydroamino acid residues, which are N-alkylated at the amino terminal nitrogen.
Tipoarticle
URIhttp://hdl.handle.net/1822/48100
DOI10.2174/2212796809999150204114112
ISSN1872-3136
Arbitragem científicayes
AcessoopenAccess
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