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Detection of the chirality of C α ‐methylated α‐amino acids with a dynamic helical poly(phenylacetylene) bearing aza‐18‐crown‐6 ether pendants
Author(s) -
Morino Kazuhide,
Kaptein Bernard,
Yashima Eiji
Publication year - 2006
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20303
Subject(s) - chemistry , phenylacetylene , chirality (physics) , norvaline , circular dichroism , amino acid , stereochemistry , helix (gastropod) , crown ether , cotton effect , enantiomer , valine , organic chemistry , biochemistry , ion , ecology , chiral symmetry breaking , physics , quantum mechanics , snail , nambu–jona lasinio model , biology , quark , catalysis
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 α ‐methylated α‐amino acids and their amide derivatives including typical meteoritic C α ‐methylated α‐amino acids such as C α ‐methyl norvaline and C α ‐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 α ‐methylated α‐amino acids. The effect of the enantiomeric excess (ee) of C α ‐methylated α‐amino acids on the helicity induction in poly‐ 1 was also investigated. Chirality, 2006. © 2006 Wiley‐Liss, Inc.