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Selection of Planar Chiral Conformations between Pillar[5,6]arenes Induced by Amino Acid Derivatives in Aqueous Media
Author(s) -
Chen Yuan,
Fu Lulu,
Sun Baobao,
Qian Cheng,
Pangannaya Srikala,
Zhu Hong,
Ma Jing,
Jiang Juli,
Ni Zhigang,
Wang Ruibing,
Lu Xiancai,
Wang Leyong
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202004003
Subject(s) - amino acid , side chain , enantiomer , chemistry , pillar , molecule , aqueous medium , carbon chain , stereochemistry , aqueous solution , ethyl ester , organic chemistry , polymer , biochemistry , structural engineering , engineering
Chiral α‐amino acids play critical roles in the metabolic process in nearly all life forms. So far, chiral recognition of α‐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 α‐side chain or ethyl ester moieties of l ‐α‐amino acid ethyl ester hydrochlorides binding with WP5 and WP6 , respectively. Therefore, α‐side chain and ethyl ester moieties of l ‐α‐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 α‐carbon of a chiral α‐amino acid molecule.