Selection of Planar Chiral Conformations between Pillar[5,6]arenes Induced by Amino Acid Derivatives in Aqueous Media

被引：26

作者：

Chen, Yuan ^{[1
]}

Fu, Lulu ^{[1
]}

Sun, Baobao ^{[1
]}

Qian, Cheng ^{[1
]}

Pangannaya, Srikala ^{[1
]}

Zhu, Hong ^{[1
]}

Ma, Jing ^{[1
]}

Jiang, Juli ^{[1
]}

Ni, Zhigang ^{[2
]}

Wang, Ruibing ^{[3
]}

Lu, Xiancai ^{[4
]}

Wang, Leyong ^{[1
,5
]}

机构：

[1] Nanjing Univ, Sch Chem & Chem Engn, Key Lab Mesoscop Chem MOE, Jiangsu Key Lab Adv Organ Mat, Nanjing 210023, Peoples R China

[2] Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 311121, Peoples R China

[3] Univ Macau, Inst Chinese Med Sci, State Key Lab Qual Res Chinese Med, Taipa, Macau, Peoples R China

[4] Nanjing Univ, Sch Earth Sci & Engn, Nanjing 210023, Peoples R China

[5] Qilu Univ Technol, Shandong Acad Sci, Adv Mat Inst, Jinan 250014, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2021年 / 27卷 / 19期

基金：

中国国家自然科学基金;

关键词：

amino acids; chiral conformations; chiral induction; chiral inversion; pillararenes;

D O I：

10.1002/chem.202004003

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chiral alpha-amino acids play critical roles in the metabolic process in nearly all life forms. So far, chiral recognition of alpha-amino acids has mainly focused on the determination of l/d enantiomers. Herein, selection of planar chiral conformations between water-soluble pillar[5]arene WP5 and pillar[6]arene WP6 was observed due to alpha-side chain or ethyl ester moieties of l-alpha-amino acid ethyl ester hydrochlorides binding with WP5 and WP6, respectively. Therefore, alpha-side chain and ethyl ester moieties of l-alpha-amino acid ethyl ester hydrochlorides were recognized by observing the induced CD signal and its inversion. This is a rare example of being able to detect the chiral region around alpha-carbon of a chiral alpha-amino acid molecule.

引用

页码：5890 / 5896

页数：7

共 35 条

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