Sugar-assisted kinetic resolution of amino acids and amplification of enantiomeric excess of organic molecules

Chemistry. 2006 Jul 17;12(21):5446-51. doi: 10.1002/chem.200600526.

Abstract

The origins of biological homochirality have intrigued researchers since Pasteur's discovery of the optical activity of biomolecules. Herein, we propose and demonstrate a novel alternative for the evolution of homochirality that is not based on autocatalysis and forges a direct relationship between the chirality of sugars and amino acids. This process provides a mechanism in which a racemic mixture of an amino acid can catalyze the formation of an optically active organic molecule in the presence of a sugar product of low enantiomeric excess.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemical synthesis
  • Alcohols / chemistry
  • Aldehydes / chemistry*
  • Amino Acids / chemistry*
  • Carbohydrates / chemistry*
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Proline / chemistry
  • Stereoisomerism

Substances

  • Alcohols
  • Aldehydes
  • Amino Acids
  • Carbohydrates
  • Proline