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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, Qian; Jin, Yingji; Huang, Haofei; Su, Zhishan; Kim, Seong Kyu; Kim, Kwan Mook
- Ewha Authors
- 김관묵
- SCOPUS Author ID
- 김관묵
- Issue Date
- 2018
- Journal Title
- BULLETIN OF THE KOREAN CHEMICAL SOCIETY
- ISSN
- 1229-5949
- Citation
- BULLETIN OF THE KOREAN CHEMICAL SOCIETY vol. 39, no. 8, pp. 960 - 964
- Keywords
- Liquid-liquid extraction; Chiral extractor; Amino acid
- Publisher
- WILEY-V C H VERLAG GMBH
- Indexed
- SCIE; 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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