Homochiral metal-organic frameworks based on amino acid ligands for HPLC separation of enantiomers

Electrophoresis. 2017 Oct;38(19):2513-2520. doi: 10.1002/elps.201700122. Epub 2017 Jul 26.

Abstract

Natural amino acids are well known to form coordination polymers with transition metal ions. In this study, six homochiral metal-organic frameworks constructed from Zn2+ or Co2+ ions and various enantiopure amino acid (L-tyrosine, L-histidine, L-tryptophan and L-glutamic acid), namely [Zn(L-tyr)]n (L-tyrZn), [Zn4 (btc)2 (Hbtc)(L-His)2 (H2 O)4 ]·1.5H2 O, {[Zn2 (L-trp)2 (bpe)2 (H2 O)2 ]·2H2 O·2NO3 }n , [Co2 (L-Trp)(INT)2 (H2 O)2 (ClO4 )], [Co2 (sdba)((L-Trp)2 ] and [Co(L-Glu)(H2 O)·H2 O] , were synthesized according to the methods previously reported in the literature. The six homochiral MOFs were explored as the chiral stationary phases for high-performance liquid chromatographic separation of enantiomers using hexane/isopropanol or hexane/dichloromethane as mobile phase. Various types of enantiomers such as alcohols, amines, ketones, ethers, organic acids, etc. can be resolved on these homochiral MOF columns. The results revealed that the enantioseletivities of homochiral MOFs based on amino acids as chiral bridging ligands used as stationary phases are practical in HPLC.

Keywords: Amino acid; Chiral separation; Chiral stationary phase; High-performance liquid chromatography; Homochiral metal-organic frameworks.

MeSH terms

  • 2-Propanol / chemistry
  • Alcohols / isolation & purification
  • Amines / isolation & purification
  • Amino Acids / chemistry*
  • Chromatography, High Pressure Liquid / instrumentation
  • Chromatography, High Pressure Liquid / methods*
  • Ethers / isolation & purification
  • Hexanes / chemistry
  • Ketones / isolation & purification
  • Metal-Organic Frameworks / chemistry*
  • Methylene Chloride / chemistry
  • Polymers / chemistry*
  • Stereoisomerism

Substances

  • Alcohols
  • Amines
  • Amino Acids
  • Ethers
  • Hexanes
  • Ketones
  • Metal-Organic Frameworks
  • Polymers
  • Methylene Chloride
  • 2-Propanol