Model dipeptides incorporating the trans cyclohexane analogues of phenylalanine: further evidence of the relationship between side-chain orientation and beta-turn type

  1. Lasa, Marta . 1
  2. Jiménez, A.I. 1
  3. Zurbano, M.M. 2
  4. Cativiela, C. 1
  1. 1 Universidad de Zaragoza
    info

    Universidad de Zaragoza

    Zaragoza, España

    ROR https://ror.org/012a91z28

  2. 2 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Aldizkaria:
Tetrahedron Letters

ISSN: 0040-4039

Argitalpen urtea: 2005

Alea: 46

Zenbakia: 48

Orrialdeak: 8377-8380

Mota: Artikulua

beta Ver similares en nube de resultados
DOI: 10.1016/J.TETLET.2005.09.155 SCOPUS: 2-s2.0-27644453392 WoS: WOS:000233214300025 GOOGLE SCHOLAR

Beste argitalpen batzuk: Tetrahedron Letters

Laburpena

In order to study the influence of the side-chain orientation on the peptide backbone conformation we have synthesised the model dipeptides t-BuCO-L-Pro-(1S,2R)-c6Phe-NHMe and t-BuCO-L-Pro-(1R,2S)-c 6Phe-NHMe, incorporating each enantiomer of the trans cyclohexane analogue of phenylalanine (trans-1-amino-2-phenylcyclohexanecarboxylic acid). The orientation of the aromatic side-chain determines the β-turn type accommodated by these peptides to the point that the (1S,2R)-c6Phe derivative retains the type I β-turn in the crystalline state, in contrast to the behaviour exhibited by the natural counterpart t-BuCO-L-Pro-L-Phe-NHMe. © 2005 Elsevier Ltd. All rights reserved.