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Enantioselective Liquid–Liquid Extraction of Underivatized Amino Acids with Simple Chiral Aminophenyl‐Aldehyde
Author(s) -
Chen Qian,
Jin Yingji,
Huang Haofei,
Su Zhishan,
Kim Seong Kyu,
Kim Kwan Mook
Publication year - 2018
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.11533
Subject(s) - imine , aldehyde , chemistry , enantioselective synthesis , hydrogen bond , extraction (chemistry) , aliquat 336 , amino acid , organic chemistry , catalysis , molecule , solvent extraction , biochemistry
The derivative of aminophenyl‐aldehyde with an asymmetric carbon and an uryl group, ( S )‐ 2 , was synthesized. The combination of ( S )‐ 2 and aliquat‐336 in CDCl 3 extracted underivatized amino acids in water layer by imine formation with enantioselectivities of 12/1 for Phe, 13/1 for Val, and 12/1 for Leu, which are comparable with those of previously reported binaphthol‐based extractor ( S )‐ 1 . The enantioselectivities of ( S )‐ 2 is remarkable considering the low molecular weight compared to ( S )‐ 1 . Density functional theory computations and experimental data demonstrate that imine bond is strengthened by resonance‐assisted hydrogen bond with the nearby NH group.