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  • Title: Detection of the chirality of C alpha-methylated alpha-amino acids with a dynamic helical poly(phenylacetylene) bearing aza-18-crown-6 ether pendants.
    Author: Morino K, Kaptein B, Yashima E.
    Journal: Chirality; 2006 Sep; 18(9):717-22. PubMed ID: 16856161.
    Abstract:
    A stereoregular poly(phenylacetylene) bearing the aza-18-crown-6 ether pendants (poly-1) was found to form a predominantly one-handed helix upon complexation with optically active C(alpha)-methylated alpha-amino acids and their amide derivatives including typical meteoritic C(alpha)-methylated alpha-amino acids such as C(alpha)-methyl norvaline and C(alpha)-methyl valine. The complexes exhibited an induced circular dichroism (ICD) in the UV-visible region of the polymer backbone. Therefore, poly-1 can be used as a novel probe for detection of the chirality of C(alpha)-methylated alpha-amino acids. The effect of the enantiomeric excess (ee) of C(alpha)-methylated alpha-amino acids on the helicity induction in poly-1 was also investigated.
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