Evaluation of amino acids as chiral ligands for the enantiodifferentiation of carbohydrates by TOCSY NMR

J Org Chem. 2010 Jun 4;75(11):3878-81. doi: 10.1021/jo1004263.

Abstract

The use of natural amino acids as chiral ligands on a triethylbenzene scaffold for the binding and enantiodifferentiation of carbohydrates has resulted in moderate affinity and selectivity values for glucose. Selective 1D TOCSY experiments revealed this as a powerful titration technology surpassing the severe overlapping of receptor and carbohydrate signals in (1)H NMR spectra.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Carbohydrate Conformation
  • Carbohydrates / chemistry*
  • Glucose / chemistry
  • Ligands
  • Magnetic Resonance Spectroscopy / methods*
  • Stereoisomerism

Substances

  • Amino Acids
  • Carbohydrates
  • Ligands
  • Glucose