Enantioselective liquid-liquid extractions of underivatized general amino acids with a chiral ketone extractant

J Am Chem Soc. 2013 Feb 20;135(7):2653-8. doi: 10.1021/ja3105945. Epub 2013 Feb 5.

Abstract

The chiral ketone (S)-3 shows high kinetic enantioselectivities toward the L form for general underivatized amino acids with hydrophobic side chains and a high thermodynamic enantioselectivity toward the D form for cysteine with its -SH polar side chain when used as an extractant in enantioselective liquid-liquid extractions in the presence of Aliquat 336. Consecutive extractions by imine formation and hydrolysis increase the enantiopurity of the amino acid, as both of these reactions are L-form-selective.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Ketones / chemistry*
  • Kinetics
  • Liquid-Liquid Extraction
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Structure
  • Quantum Theory*
  • Stereoisomerism
  • Thermodynamics

Substances

  • Amino Acids
  • Ketones