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.
Mazaleyrat
Jean-Paul
JP
Contribution from SIRCOB, UMR CNRS 8086, Bâtiment Lavoisier, University of Versailles, F-78035 Versailles, France.
Wright
Karen
K
Gaucher
Anne
A
Toulemonde
Nathalie
N
Wakselman
Michel
M
Oancea
Simona
S
Peggion
Cristina
C
Formaggio
Fernando
F
Setnicka
Vladimir
V
Keiderling
Timothy A
TA
Toniolo
Claudio
C
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