On the role of DNA in DNA-based catalytic enantioselective conjugate addition reactions

Org Biomol Chem. 2010 Sep 7;8(17):3868-73. doi: 10.1039/c005048b. Epub 2010 Jun 25.

Abstract

A kinetic study of DNA-based catalytic enantioselective Friedel-Crafts alkylation and Michael addition reactions showed that DNA affects the rate of these reactions significantly. Whereas in the presence of DNA, a large acceleration was found for the Friedel-Crafts alkylation and a modest acceleration in the Michael addition of dimethyl malonate, a deceleration was observed when using nitromethane as nucleophile. Also, the enantioselectivities proved to be dependent on the DNA sequence. In comparison with the previously reported Diels-Alder reaction, the results presented here suggest that DNA plays a similar role in both cycloaddition and conjugate addition reactions.

MeSH terms

  • Alkylation
  • Catalysis
  • DNA / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • DNA