Detection and Amplification of a Small Enantiomeric Imbalance in α-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) wit...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2003-02, Vol.125 (5), p.1278-1283
Main Authors: Nonokawa, Ryuji, Yashima, Eiji
Format: Article
Language:English
Subjects:
Acetylene - analogs & derivatives
Acetylene - chemistry
Amino Acids - chemistry
Amino Alcohols - chemistry
Applied sciences
Circular Dichroism
Ethers, Cyclic - chemistry
Exact sciences and technology
Models, Molecular
Organic polymers
Physicochemistry of polymers
Polymers - chemistry
Properties and characterization
Stereoisomerism
Structure, morphology and analysis
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Summary: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 α-amino acids (less than 0.005% enantiomeric excess of alanine, for example).
ISSN:0002-7863
1520-5126
DOI:10.1021/ja028348c