Absolute Configurational Assignments of Amino Acid Esters by a CD-Sensitive Malonamide-Linked Zinc Bisporphyrinate Host

Authors

  • Baozhen Liu,

    1. Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu 215123, China
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  • Jiaxun Jiang,

    1. Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu 215123, China
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  • Xianshi Fang,

    1. Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu 215123, China
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  • Chuanjiang Hu

    Corresponding author
    1. Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu 215123, China
    2. State Key Lab & Coordination Chemistry Institute, Nanjing University, Nanjing, Jiangsu 210093, China
    • Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu 215123, China

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Abstract

A novel malonamide-linked zinc bisporphyrinate [Zn2-1] has been designed and synthesized. UV-vis and NMR spectroscopic studies suggest the molecule aggregates in solution. Such zinc bisporphyrinate is very CD-sensitive when it is mixed with amino acid ethyl esters. The amplitude value of the induced circular dichroism (ICD) is up to ca. 1500 L·mol−1·cm−1. Further studies by 1H NMR and UV-vis spectroscopies reveal amino acid esters function as monodentate ligands, and [Zn2-1] interacts with amino acid ethyl esters through coordination and hydrogen bonding interactions.

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