Utilize este identificador para referenciar este registo:
https://hdl.handle.net/1822/18083
Título: | Straightforward, racemization-free synthesis of peptides with fairly to very bulky di- and trisubstituted glycines |
Autor(es): | Pinto, Filipa C. S. C. Lima, Sílvia M. M. A. Pereira Maia, Hernâni L. S. |
Palavras-chave: | A,a-Dialkylglycines N,a,a-Trialkylglycines Peptide synthesis Ugi–passerini reaction |
Data: | Nov-2009 |
Editora: | Elsevier 1 |
Revista: | Tetrahedron |
Resumo(s): | Several fully protected tri- and pentapeptides containing a central symmetrical α,α-dialkyl glycine residue, with the alkyl group varying from methyl or ethyl to benzyl, were synthesized in good yields by a strategy based on the Ugi–Passerini reaction. Each Ugi–Passerini adduct was selectively cleaved and the product submitted to an assisted N,N′-dicyclohehylcarbodiimide coupling to an amino acid or dipeptide ester, respectively. Tripeptides as the above but containing a 4-methoxybenzyl group at the nitrogen atom of the central residue were also synthesized in fair to good yields by N-[(1H-benzotriazol-1-yl)-(dimethylamino)methylene]-N-methylmethanaminium hexafluorophosphate N-oxide assisted couplings. The results reported here show that our strategy is appropriate for routine synthesis of peptides incorporating these moieties. |
Tipo: | Artigo |
URI: | https://hdl.handle.net/1822/18083 |
DOI: | 10.1016/j.tet.2009.09.022 |
ISSN: | 0040-4020 |
Versão da editora: | http://www.sciencedirect.com/science?_ob=MiamiImageURL&_cid=271372&_user=2459786&_pii=S0040402009013696&_check=y&_origin=search&_coverDate=07-Nov-2009&view=c&wchp=dGLzVlt-zSkzS&md5=0bef43cbc6ee7df0531210bce8ec5749/1-s2.0-S0040402009013696-main.pdf |
Arbitragem científica: | yes |
Acesso: | Acesso restrito UMinho |
Aparece nas coleções: | CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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1 Main Text.pdf Acesso restrito! | texto do artigo | 234,68 kB | Adobe PDF | Ver/Abrir |
2 Tables.pdf Acesso restrito! | tabelas | 29,49 kB | Adobe PDF | Ver/Abrir |
3 Scheme.cdx Acesso restrito! | esquema | 23,7 kB | chemDraw | Ver/Abrir |
5 Scheme 2.cdx Acesso restrito! | esquema | 23,97 kB | chemDraw | Ver/Abrir |