Enantioselective CD analysis of amino acids based on chiral amplification with a stereodynamic probe

被引：26

作者：

Ghosn, Marwan W. ^{[1
]}

Wolf, Christian ^{[1
]}

机构：

[1] Georgetown Univ, Dept Chem, Washington, DC 20057 USA

来源：

TETRAHEDRON | 2010年 / 66卷 / 23期

关键词：

Amino acids; Sensing; Chiral amplification; Circular dichroism; Dynamic stereochemistry; INDICATOR DISPLACEMENT ASSAYS; INDUCED AXIAL CHIRALITY; ENANTIOMERIC EXCESS; FLUORESCENT RECOGNITION; ABSOLUTE-CONFIGURATION; COPPER(II) COMPLEX; CIRCULAR-DICHROISM; CARBOXYLIC-ACIDS; BIPHENYL CORE; RESIDUE BIP;

D O I：

10.1016/j.tet.2010.04.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The condensation between stereolabile 1,8-bis(3'-formy1-4'-hydroxyphenyl)naphthalene, 1, and two amino acid molecules results in the formation of chiral diimines exhibiting strong CD signals. This reaction has been used to develop a chiroptical sensing method for the determination of the absolute configuration and enantiomeric composition of unprotected amino acids. This sensing approach is based on distinctive chiral amplification due to central-to-axial chirality induction within the diimine scaffold formed and does not require the use of an enantiopure ligand or metal complex. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：3989 / 3994

页数：6

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