以γ-环糊精作为手性选择剂，基于显著的室温磷光寿命差异对奎宁和奎尼丁进行手性识别。

Chiral discrimination of quinine and quinidine based on notable room temperature phosphorescence lifetime differences with gamma-cyclodextrin as chiral selector.

作者信息

Zhang Xiao Hua, Wang Yu, Jin Wei Jun

机构信息

School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, PR China.

出版信息

Talanta. 2007 Oct 31;73(5):938-42. doi: 10.1016/j.talanta.2007.05.014. Epub 2007 May 21.

DOI:10.1016/j.talanta.2007.05.014

PMID:19073124

Abstract

Upon addition of small amount of bromocyclohexane (BrCH), quinine (QN) and quinidine (QD) display strong room temperature phosphorescence (RTP) in gamma-cyclodextrin (gamma-CD) solution without deoxygenation. The associated phosphorescence decay curves can be best fitted to biexponential patterns and quite different RTP lifetimes are obtained for QN (86.9 and 12.5ms) and QD (12.1 and 4.17ms), indicating a distinct chiral discrimination of gamma-CD toward this pair of pseudo-enantiomers. The corresponding association constants evaluated for QN/gamma-CD/BrCH and QD/gamma-CD/BrCH are 3.47x10(5) and 4.67x10(4)Lmol(-1), respectively. It can be inferred that their different ability to form complexes with the chiral gamma-CD is accounted for the notable difference in RTP lifetimes between QN and QD.

摘要

加入少量溴代环己烷（BrCH）后，奎宁（QN）和奎尼丁（QD）在γ-环糊精（γ-CD）溶液中无需脱氧即可呈现强烈的室温磷光（RTP）。相关的磷光衰减曲线能很好地拟合为双指数模式，并且奎宁（86.9和12.5毫秒）和奎尼丁（12.1和4.17毫秒）获得了截然不同的RTP寿命，这表明γ-CD对这一对假对映体具有明显的手性识别能力。针对QN/γ-CD/BrCH和QD/γ-CD/BrCH评估得到的相应缔合常数分别为3.47×10⁵和4.67×10⁴L·mol⁻¹。可以推断，它们与手性γ-CD形成络合物的能力不同，这是奎宁和奎尼丁RTP寿命存在显著差异的原因。