Chiral Selective Chemistry Induced by Natural Selection of Spin-Polarized Electrons

Angew Chem Int Ed Engl. 2015 Jun 15;54(25):7295-8. doi: 10.1002/anie.201501678. Epub 2015 May 7.

Abstract

The search to understand the origin of homochirality in nature has been ongoing since the time of Pasteur. Previous work has shown that DNA can act as a spin filter for low-energy electrons and that spin-polarized secondary electrons produced by X-ray irradiation of a magnetic substrate can induce chiral selective chemistry. In the present work it is demonstrated that secondary electrons from a substrate that are transmitted through a chiral overlayer cause enantiomeric selective chemistry in an adsorbed adlayer. We determine the quantum yields (QYs) for dissociation of (R)- or (S)-epichlorohydrin adsorbed on a chiral self-assembled layer of DNA on gold and on bare gold (for control). The results show that there is a significant difference in the QYs between the two enantiomers when adsorbed on DNA, but none when they are adsorbed on bare Au. We propose that the effect results from natural spin filtering effects cause by the chiral monolayer.

Keywords: DNA; chirality; enantioselectivity; photoelectron spectroscopy; surface chemistry.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Adsorption
  • Chlorohydrins / chemistry*
  • Electrons
  • Gold / chemistry
  • Immobilized Nucleic Acids / chemistry*
  • Models, Molecular
  • Photoelectron Spectroscopy
  • Stereoisomerism
  • Surface Properties
  • X-Rays

Substances

  • Chlorohydrins
  • Immobilized Nucleic Acids
  • Gold