King Eric D, Tao Peng, Sanan Toby T, Hadad Christopher M, Parquette Jon R
Department of Chemistry, The Ohio State University, Columbus, OH 43210, USA.
Org Lett. 2008 May 1;10(9):1671-4. doi: 10.1021/ol8004722. Epub 2008 Apr 9.
Appending L-alanine to the terminal positions of a helical azobenzene oligomer produced a P helical bias, which increased with oligomer length. Irradiation gave rise to E-->Z isomerization of the terminal azo linkages, which displaced the stereogenic center of L-Ala from the helix backbone and suppressed chiral induction. Theoretical simulations of the CD spectrum of the P helical conformation are in qualitative agreement with the experimental spectra.
在螺旋状偶氮苯低聚物的末端位置连接L-丙氨酸会产生P螺旋偏向性,这种偏向性会随着低聚物长度的增加而增强。辐照会导致末端偶氮键发生E→Z异构化,这使得L-丙氨酸的手性中心从螺旋主链上移位并抑制了手性诱导。P螺旋构象的圆二色光谱的理论模拟与实验光谱在定性上是一致的。