Induced Axial Chirality in the Biphenyl Core of the Proatropoisomeric, C α ‐Tetrasubstituted α‐Amino Acid Residue Bip in Peptides - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2005

Induced Axial Chirality in the Biphenyl Core of the Proatropoisomeric, C α ‐Tetrasubstituted α‐Amino Acid Residue Bip in Peptides

Résumé

Abstract An induced axial chirality in the biphenyl core of the 2′,1′:1,2;1′′,2′′:3,4‐dibenzcyclohepta‐1,3‐diene‐6‐amino‐6‐carboxylic acid (Bip) residue, a conformationally labile, atropoisomeric, C α ‐tetrasubstituted α‐amino acid, was observed by CD and 1 H NMR spectroscopic techniques in the linear dipeptides Boc‐Bip‐Xaa*‐OMe where Boc= tert ‐butoxycarbonyl, OMe=methoxy, and Xaa*= D ‐ and/or L ‐ Ala, ‐Val, ‐Leu, ‐Phe, ‐(αMe)Val and ‐(αMe)Leu. Chiral induction was significantly lower in the isomeric dipeptides Boc‐Xaa*‐Bip‐OMe, with the Xaa* residue located at the N‐terminus of Bip, as well as in the cyclic dipeptide cyclo‐[Bip‐ L ‐ Ala]. The results obtained in solution were confirmed by X‐ray diffraction analysis of a crystalline sample of Boc‐( R )‐Bip‐ D ‐Ala‐OMe.

Domaines

Chimie

Dates et versions

hal-04429471 , version 1 (31-01-2024)

Identifiants

Citer

Jean‐paul Mazaleyrat, Karen Wright, Anne Gaucher, Nathalie Toulemonde, Laurence Dutot, et al.. Induced Axial Chirality in the Biphenyl Core of the Proatropoisomeric, C α ‐Tetrasubstituted α‐Amino Acid Residue Bip in Peptides. Chemistry - A European Journal, 2005, 11 (23), pp.6921-6929. ⟨10.1002/chem.200500187⟩. ⟨hal-04429471⟩

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