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

Qian Chen, Yingji Jin, Haofei Huang, Zhishan Su, Seong Kyu Kim, Kwan Mook Kim

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

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.

Original languageEnglish
Pages (from-to)960-964
Number of pages5
JournalBulletin of the Korean Chemical Society
Volume39
Issue number8
DOIs
StatePublished - Aug 2018

Keywords

  • Amino acid
  • Chiral extractor
  • Liquid–liquid extraction

Fingerprint

Dive into the research topics of 'Enantioselective Liquid–Liquid Extraction of Underivatized Amino Acids with Simple Chiral Aminophenyl-Aldehyde'. Together they form a unique fingerprint.

Cite this