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Enantioselective Liquid-Liquid Extraction of Underivatized Amino Acids with Simple Chiral Aminophenyl-Aldehyde

Title
Enantioselective Liquid-Liquid Extraction of Underivatized Amino Acids with Simple Chiral Aminophenyl-Aldehyde
Authors
Chen, QianJin, YingjiHuang, HaofeiSu, ZhishanKim, Seong KyuKim, Kwan Mook
Ewha Authors
김관묵
SCOPUS Author ID
김관묵scopus
Issue Date
2018
Journal Title
BULLETIN OF THE KOREAN CHEMICAL SOCIETY
ISSN
1229-5949JCR Link
Citation
BULLETIN OF THE KOREAN CHEMICAL SOCIETY vol. 39, no. 8, pp. 960 - 964
Keywords
Liquid-liquid extractionChiral extractorAmino acid
Publisher
WILEY-V C H VERLAG GMBH
Indexed
SCIE; SCOPUS WOS scopus
Document Type
Article
Abstract
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 CDCl3 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.
DOI
10.1002/bkcs.11533
Appears in Collections:
자연과학대학 > 화학·나노과학전공 > Journal papers
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