Detection and amplification of a small enantiomeric imbalance in alpha-amino acids by a helical poly(phenylacetylene) with crown ether pendants.
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).
Nonokawa
Ryuji
R
Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan.
Yashima
Eiji
E
D000114:Acetylene / Q000031:analogs & derivatives* / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D000605:Amino Alcohols / Q000737:chemistry; D002942:Circular Dichroism; D004988:Ethers, Cyclic / Q000737:chemistry*; D008958:Models, Molecular; D011108:Polymers / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D000605:Amino Alcohols; D004988:Ethers, Cyclic; D011108:Polymers; C044736:phenylacetylene; D000114:Acetylene