Chiral Induction and Remote Chiral Communication in Quinoline Oligoamide Foldamers for Determination of Enantiomeric Excess and Absolute Configuration of Chiral Amines and Their Derivatives.,Chemistry - A European Journal

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Chiral Induction and Remote Chiral Communication in Quinoline Oligoamide Foldamers for Determination of Enantiomeric Excess and Absolute Configuration of Chiral Amines and Their Derivatives.
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2019-10-09 , DOI: 10.1002/chem.201903032
Lu Zheng _{1,

2,

3} , Yulin Zhan ₄ , Lin Ye ₄ , Dan Zheng ₄ , Ying Wang ₄ , Kun Zhang _{1,

2} , Hua Jiang _{1,

2,

4}

Affiliation

Two pentameric foldamers, Q5 and Q5C-S, containing a C-F bond were synthesized based on quinoline oligamide foldamers for the measurement of enantiomeric excess and for the determination of absolute configuration of chiral amines, diamines, amino alcohols, and α-amino acid esters. Chiral induction of Q5 was triggered in situ when the chiral analytes reacted with the C-F bond in Q5 by a N-nucleophilic substitution reaction, leading to a linear correlation between the CD amplitude at the region of quinoline chromophores and the ee values of the chiral analytes, which can be used for the ee determination of chiral analytes. Furthermore, the CD intensity of Q5C-S containing a chiral motif at its C-terminus enhances via remote, favorable chiral communication when the chiral induction was triggered in situ by chiral analytes at the N-terminus matches the original helicity of Q5C-S, but decreases via remote, conflicted chiral communication when the chiral induction is triggered in situ by chiral molecules at the N-terminus mismatches the original one. The system can thus be used for determination of the absolute configuration of chiral analytes, given that the chirality of the chiral motif at the C-terminus of Q5C-S is known.

中文翻译：

喹啉低聚酰胺折叠剂中的手性诱导和远程手性交流，用于确定手性胺及其衍生物的对映体过量和绝对构型。

基于喹啉低酰胺折叠剂，合成了两个包含CF键的五聚体折叠剂Q5和Q5C-S，用于测量对映体过量和确定手性胺，二胺，氨基醇和α-氨基酸酯的绝对构型。当手性分析物通过N-亲核取代反应与Q5中的CF键反应时，就地触发了Q5的手性诱导，导致喹啉发色团区域的CD振幅与手性分析物的ee值之间呈线性相关，可用于手性分析物的ee测定。此外，Q5C-S在其C末端包含一个手性基序的CD强度会通过远程，当N端的手性分析物原位触发手性诱导时，有利的手性交流与Q5C-S的原始螺旋度相符，但当N处的手性分子原位触发手性诱导时，通过远程冲突的手性交流而降低-末端与原始末端不匹配。假定已知Q5C-S的C端的手性基序的手性，该系统可用于确定手性分析物的绝对构型。

更新日期：2019-10-10

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