通过带有冠醚侧基的螺旋状聚（苯乙炔）检测和放大α-氨基酸中的微小对映体失衡。

Detection and amplification of a small enantiomeric imbalance in alpha-amino acids by a helical poly(phenylacetylene) with crown ether pendants.

作者信息

Nonokawa Ryuji, Yashima Eiji

机构信息

Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan.

出版信息

J Am Chem Soc. 2003 Feb 5;125(5):1278-83. doi: 10.1021/ja028348c.

DOI:10.1021/ja028348c

PMID:12553829

Abstract

We have designed a novel stereoregular poly(phenylacetylene) bearing the bulky crown ether as the pendant (poly-1) for the amino acid binding site. The polymer forms a one-handed helix upon complexation with l-amino acid perchlorates, and the complexes exhibit an induced circular dichroism (ICD) with the same Cotton effect signs in the polymer backbone region through a significant cooperative interaction. Poly-1 is highly sensitive to the amino acid chirality and can detect an extremely small enantiomeric imbalance in alpha-amino acids (less than 0.005% enantiomeric excess of alanine, for example).

摘要

我们设计了一种新型的立体规整聚（苯乙炔），其带有庞大的冠醚作为侧基（聚-1）用于氨基酸结合位点。该聚合物与L-氨基酸高氯酸盐络合时形成单手螺旋，并且通过显著的协同相互作用，络合物在聚合物主链区域表现出具有相同科顿效应符号的诱导圆二色性（ICD）。聚-1对氨基酸手性高度敏感，能够检测α-氨基酸中极其微小的对映体失衡（例如，丙氨酸的对映体过量小于0.005%）。