( S )-ABOC: A Rigid Bicyclic β-Amino Acid as Turn Inducer

Christophe Andre (1) , Baptiste Legrand (2) , Cheng Deng (3) , Claude Didierjean (4) , Guillaume Pickaert (3) , Jean Martinez (1) , Marie Christine Averlant-Petit (3) , Muriel Amblard (5, 1) , Monique Calmes (1)

1 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]
2 ICM - Interactions cellulaires et moléculaires
3 LCPM - Laboratoire de Chimie Physique Macromoléculaire
4 CRM2 - Cristallographie, Résonance Magnétique et Modélisations
5 laboratoire de chimie et pharmacologie de molécules d'intérêt biologique

In order to investigate the ability of the (S)-aminobicyclo[2.2.2]octane-2-carboxylic acid 1 (H-(S)-ABOC-OH) to induce reverse turns into peptides, two model tripeptides, in which this bicyclic unit was incorporated into the second position, were synthesized and analyzed by FT-IR, CD, NMR, and X-ray studies.

Domains: Chemical Sciences

Christophe Andre, Baptiste Legrand, Cheng Deng, Claude Didierjean, Guillaume Pickaert, et al.. ( S )-ABOC: A Rigid Bicyclic β-Amino Acid as Turn Inducer. Organic Letters, 2012, 14 (4), pp.960 - 963. ⟨10.1021/ol203406v⟩. ⟨hal-01629815⟩