ß-turn modulation by the incorporation of c6Ser into Xaa-Pro dipeptide
- Avenoza, A. 1
- Busto, J.H. 1
- Cativiela, C. 2
- Peregrina, J.M. 1
- Rodríguez, F. 1
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1
Universidad de La Rioja
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2
Instituto de Nanociencia y Materiales de Aragón
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ISSN: 0040-4039
Ano de publicación: 2002
Volume: 43
Número: 8
Páxinas: 1429-1432
Tipo: Artigo
beta Ver similares en nube de resultadosOutras publicacións en: Tetrahedron Letters
Resumo
The enantiomerically pure (1R,2S)- and (1S,2R)-1-amino-2-hydroxycyclohexane-1-carboxylic acids (c6Ser) 1 and 2 were incorporated into dipeptide Xaa-Pro by a resolution method, involving the aminolysis of a racemic 2-tert-butyl-5(4H)-oxazolone intermediate with the hydrochloride derivative of L-Pro-NHMe. Once the model dipeptides Piv-(1R,2S)-c6Ser-L-Pro-NHMe (6) and Piv-(1S,2R)-c6Ser-L-Pro-NHMe (7) were formed and separated, their X-ray analysis allowed the characterisation of a non-folded structure for peptide 6 and an unexpected type I β-turn with a trans-Pro at the i+2 position for peptide 7. © 2002 Elsevier Science Ltd. All rights reserved.