Detection of the chirality of Cα‐methylated α‐amino acids with a dynamic helical poly(phenylacetylene) bearing aza‐18‐crown‐6 ether pendants
Detection of the chirality of Cα‐methylated α‐amino acids with a dynamic helical poly(phenylacetylene) bearing aza‐18‐crown‐6 ether pendants
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DOI：
10.1002/chir.20303
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发表时间：
2006
期刊：
影响因子：
2
通讯作者：
K. Morino;B. Kaptein;E. Yashima
中科院分区：
文献类型：
--
作者：
K. Morino;B. Kaptein;E. Yashima
在与具有光学活性的C(α)-甲基化α -氨基酸及其酰胺衍生物(包括典型的C(α)-甲基化α -氨基酸如C（α)-甲基正缬氨酸和C(α)-甲基缬氨酸）络合后，发现含有氮杂-18-冠-6醚垂链（poly-1）的立体规则聚（苯乙炔）形成主要的单手螺旋。该配合物在聚合物主链的紫外可见区表现出诱导的圆二色性（ICD）。因此，poly-1可以作为检测C（α）甲基化α -氨基酸手性的新探针。研究了C（α）甲基化α -氨基酸对映体过量（ee）对poly-1螺旋诱导的影响。
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.