A Racemic Naphthyl-Coumarin-Based Probe for Quantitative Enantiomeric Excess Analysis of Amino Acids and Enantioselective Sensing of Amines and Amino Alcohols

ChemistryOpen. 2022 Jun;11(6):e202200088. doi: 10.1002/open.202200088.

Abstract

A new racemic naphthyl-coumarin-based probe was found to bind covalently with amino acids in MeOH-KOH system and thereby generates distinct CD responses. The induced strong CD signals allowed quantitative enantiomeric excess analysis of amino acids and enantioselective sensing of amines and amino alcohols. The mechanism for the reaction of the coumarin-aldehyde probe with an amino acid was investigated by CD, UV-Vis, NMR, ESI-MS analyses and ECD calculation.

Keywords: chiral amine; circular dichroism; enantioselective recognition; naphthyl-coumarin; racemic probe.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines* / chemistry
  • Amino Acids / chemistry
  • Amino Alcohols* / chemistry
  • Coumarins
  • Stereoisomerism

Substances

  • Amines
  • Amino Acids
  • Amino Alcohols
  • Coumarins