Detection and amplification of a small enantiomeric imbalance in alpha-amino acids by a helical poly(phenylacetylene) with crown ether pendants

J Am Chem Soc. 2003 Feb 5;125(5):1278-83. doi: 10.1021/ja028348c.

Abstract

We have designed a novel stereoregular poly(phenylacetylene) bearing the bulky crown ether as the pendant (poly-1) for the amino acid binding site. The polymer forms a one-handed helix upon complexation with l-amino acid perchlorates, and the complexes exhibit an induced circular dichroism (ICD) with the same Cotton effect signs in the polymer backbone region through a significant cooperative interaction. Poly-1 is highly sensitive to the amino acid chirality and can detect an extremely small enantiomeric imbalance in alpha-amino acids (less than 0.005% enantiomeric excess of alanine, for example).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylene / analogs & derivatives*
  • Acetylene / chemistry*
  • Amino Acids / chemistry*
  • Amino Alcohols / chemistry
  • Circular Dichroism
  • Ethers, Cyclic / chemistry*
  • Models, Molecular
  • Polymers / chemistry
  • Stereoisomerism

Substances

  • Amino Acids
  • Amino Alcohols
  • Ethers, Cyclic
  • Polymers
  • phenylacetylene
  • Acetylene