ß-turn modulation by the incorporation of c6Ser into Xaa-Pro dipeptide

  1. Avenoza, A. 1
  2. Busto, J.H. 1
  3. Cativiela, C. 2
  4. Peregrina, J.M. 1
  5. Rodríguez, F. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

  2. 2 Instituto de Nanociencia y Materiales de Aragón
    info

    Instituto de Nanociencia y Materiales de Aragón

    Zaragoza, España

    ROR https://ror.org/031n2c920

Revista:
Tetrahedron Letters

ISSN: 0040-4039

Año de publicación: 2002

Volumen: 43

Número: 8

Páginas: 1429-1432

Tipo: Artículo

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DOI: 10.1016/S0040-4039(02)00030-8 SCOPUS: 2-s2.0-0037127571 WoS: WOS:000174116000019 GOOGLE SCHOLAR

Otras publicaciones en: Tetrahedron Letters

Resumen

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.