Detection of the chirality of C alpha-methylated alpha-amino acids with a dynamic helical poly(phenylacetylene) bearing aza-18-crown-6 ether pendants.
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.
Morino
Kazuhide
K
Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya, Japan.
Kaptein
Bernard
B
Yashima
Eiji
E
D000114:Acetylene / Q000031:analogs & derivatives* / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D002942:Circular Dichroism; D043844:Crown Ethers / Q000737:chemistry*; D004988:Ethers, Cyclic / Q000737:chemistry*; D008958:Models, Molecular; D013237:Stereoisomerism
D000596:Amino Acids; D043844:Crown Ethers; D004988:Ethers, Cyclic; C456584:aza-18-crown-6 ether; C044736:phenylacetylene; D000114:Acetylene