Enantioselective Liquid-Liquid Extraction of Underivatized Amino Acids with Simple Chiral Aminophenyl-Aldehyde
- 주제(키워드) Liquid-liquid extraction , Chiral extractor , Amino acid
- 주제(기타) Chemistry, Multidisciplinary
- 설명문(일반) [Chen, Qian; Jin, Yingji; Kim, Kwan Mook] Ewha Womans Univ, Dept Chem & Nano Sci, Biochiral Lab, Seoul 03760, South Korea; [Huang, Haofei] Shandong Univ Technol, Coll Chem Engn, Zibo 255049, Peoples R China; [Su, Zhishan] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Sichuan, Peoples R China; [Kim, Seong Kyu] Sungkyunkwan Univ, Dept Chem, Gyeong Gi Do 16419, South Korea
- 등재 SCIE, SCOPUS
- 발행기관 WILEY-V C H VERLAG GMBH
- 발행년도 2018
- URI http://www.dcollection.net/handler/ewha/000000156076
- 본문언어 영어
- Published As http://dx.doi.org/10.1002/bkcs.11533
초록/요약
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.
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