Induced axial chirality in the biphenyl core of the Calpha-tetrasubstituted alpha-amino acid residue Bip and subsequent propagation of chirality in (Bip)n/Val oligopeptides.
In the dipeptides Boc-Bip-L-Val-OMe and Boc-Bip-D-Val-OMe, an induced axial chirality in the biphenyl core of the Bip residue, a conformationally labile, proatropoisomeric C(alpha,alpha)-disubstituted glycine, was observed by electronic CD and (1)H NMR. Chiral induction is significantly higher when the Val residue is located at the C-terminal position of Bip. An outstanding phenomenon of propagation of chirality was demonstrated to occur in the related 3(10)-helical -(Bip)n-L-Val (n = 2-6) oligopeptides by CD and vibrational CD techniques.
Contribution from SIRCOB, UMR CNRS 8086, Bâtiment Lavoisier, University of Versailles, F-78035 Versailles, France.
Jean-Paul
JP
Mazaleyrat
Karen
K
Wright
Anne
A
Gaucher
Nathalie
N
Toulemonde
Michel
M
Wakselman
Simona
S
Oancea
Cristina
C
Peggion
Fernando
F
Formaggio
Vladimir
V
Setnicka
Timothy A
TA
Keiderling
Claudio
C
Toniolo
D000596:Amino Acids / Q000737:chemistry*; D001713:Biphenyl Compounds / Q000737:chemistry*; D002942:Circular Dichroism; D004151:Dipeptides / Q000737:chemistry; D009842:Oligopeptides / Q000138:chemical synthesis / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism; D014633:Valine / Q000737:chemistry
D000596:Amino Acids; D001713:Biphenyl Compounds; D004151:Dipeptides; D009842:Oligopeptides; D014633:Valine