293767-95-0Relevant academic research and scientific papers
A γ-turn induced by a highly constrained cyclopropane analogue of phenylalanine (c3diPhe) in the solid state
Jiménez, Ana I.,Cativiela, Carlos,Marraud, Michel
, p. 5353 - 5356 (2000)
In order to evaluate the possible influence of the side chain orientation on the backbone conformation we have synthesized the model dipeptides (t)BuCO-L-Pro-c3diPhe-NH(i)Pr, where c3diPhe represents (2S, 3S)-and (2R,3R)-1-amino-2,3-diphenylcyclopropanecarboxylic acid, two cyclopropane analogues of phenylalanine. In the solid state, the (2S,3S)c3diPhe-containing compound adopts a classical βII-turn disposition. In contrast, the dipeptide incorporating the (2R,3R) enantiomer exhibits an open βII-turn structure that lacks the usual i+3 to i hydrogen bond, together with a γ-turn centred at the c3diPhe residue. (C) 2000 Elsevier Science Ltd.
