Allosteric P═O-based receptors for dicarboxylic acids

Org Lett. 2011 Jul 15;13(14):3632-5. doi: 10.1021/ol201277d. Epub 2011 Jun 13.

Abstract

The synthesis of new P═O-disubstituted receptors with appended crown ethers and their properties as receptors for dicarboxylic acids have been studied. High affinities have been observed (oxalic and malonic acids with 4-, 5-, 6-, or 8-crown ethers). Binding of a cationic effector within the crown ether unit resulted in a positive "allosteric" effect, which has been determined to be K(rel) = 7 in the best case (binding of malonic acid with Li(+) @ rac-3b).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crown Ethers / chemical synthesis
  • Crown Ethers / chemistry
  • Crystallography, X-Ray
  • Dicarboxylic Acids / chemistry*
  • Malonates / chemistry
  • Molecular Conformation
  • Oxalic Acid / chemistry
  • Oxazines
  • Pyrimidines

Substances

  • Crown Ethers
  • Dicarboxylic Acids
  • Malonates
  • Oxazines
  • Pyrimidines
  • 6H,8H-3,4-dihydropyrimido(4,5-c)(1,2)oxazin-7-one
  • Oxalic Acid
  • malonic acid