Mazaleyrat Jean-Paul, Wright Karen, Gaucher Anne, Toulemonde Nathalie, Wakselman Michel, Oancea Simona, Peggion Cristina, Formaggio Fernando, Setnicka Vladimir, Keiderling Timothy A, Toniolo Claudio
Contribution from SIRCOB, UMR CNRS 8086, Bâtiment Lavoisier, University of Versailles, F-78035 Versailles, France.
J Am Chem Soc. 2004 Oct 13;126(40):12874-9. doi: 10.1021/ja040100v.
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.
在二肽Boc-Bip-L-Val-OMe和Boc-Bip-D-Val-OMe中，通过电子圆二色光谱（electronic CD）和氢核磁共振（¹H NMR）观察到，在Bip残基的联苯核心中诱导产生了轴向手性，Bip残基是一种构象不稳定的原轴手性C(α,α)-二取代甘氨酸。当Val残基位于Bip的C末端位置时，手性诱导作用明显更强。通过圆二色光谱（CD）和振动圆二色光谱（vibrational CD）技术证明，在相关的3(10)-螺旋-(Bip)n-L-Val（n = 2 - 6）寡肽中发生了显著的手性传递现象。
