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

Autor: Chen Y; Key Laboratory of Mesoscopic Chemistry of MOE, Jiangsu, Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, P. R. China., Fu L; Key Laboratory of Mesoscopic Chemistry of MOE, Jiangsu, Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, P. R. China., Sun B; Key Laboratory of Mesoscopic Chemistry of MOE, Jiangsu, Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, P. R. China., Qian C; Key Laboratory of Mesoscopic Chemistry of MOE, Jiangsu, Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, P. R. China., Pangannaya S; Key Laboratory of Mesoscopic Chemistry of MOE, Jiangsu, Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, P. R. China., Zhu H; Key Laboratory of Mesoscopic Chemistry of MOE, Jiangsu, Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, P. R. China., Ma J; Key Laboratory of Mesoscopic Chemistry of MOE, Jiangsu, Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, P. R. China., Jiang J; Key Laboratory of Mesoscopic Chemistry of MOE, Jiangsu, Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, P. R. China., Ni Z; College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, 311121, P. R. China., Wang R; State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Taipa, Macau, P. R. China., Lu X; School of Earth Science and Engineering, Nanjing University, Nanjing, 210023, P. R. China., Wang L; Key Laboratory of Mesoscopic Chemistry of MOE, Jiangsu, Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, P. R. China.; Advanced Materials Institute, Qilu University of Technology, (Shandong Academy of Sciences), Jinan, 250014, P. R. China.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2021 Apr 01; Vol. 27 (19), pp. 5890-5896. Date of Electronic Publication: 2021 Mar 15.
DOI: 10.1002/chem.202004003
Abstrakt: 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.
(© 2020 Wiley-VCH GmbH.)
Databáze: MEDLINE
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