Chiroptical sensing of amino acids by stereodynamic imprinting into the Zn-II-Complex generating a dihedral chirality
- 주제(키워드) Circular dichroism amplification , Absolute configuration of amino acid , Enantiomeric excess determination , Dihedral chirality , Stereodynamic imprinting
- 주제(기타) Chemistry, Applied; Engineering, Chemical; Materials Science, Textiles
- 설명문(일반) [Chen, Qian; Shirbhate, Mukesh Eknath; Kim, Youngmee; Kim, Sung-Jin; Kim, Kwan Mook] Ewha Womans Univ, Dept Chem & Nano Sci, Seoul 03760, South Korea; [Kang, Baotao] Univ Jinan, Sch Chem & Chem Engn, Jinan 250022, Shandong, Peoples R China
- 등재 SCIE, SCOPUS
- 발행기관 ELSEVIER SCI LTD
- 발행년도 2019
- URI http://www.dcollection.net/handler/ewha/000000159673
- 본문언어 영어
- Published As http://dx.doi.org/10.1016/j.dyepig.2019.01.007
초록/요약
A stereodynamic chiroptical sensor based on three-component assembly of 3-(di-2-picolylaminoacetamido)-2-formyl-naphthalene (1), Zn-II and amino acids was developed. The imine formed between 1 and an amino acid has six coordination sites to bind tightly ZIP ion. The crystal structure of the Zn-II complex, 1-Zn-D-Phe, revealed that the naphthyl ring is tilted to one pyridine ring to generate axial chirality. The dihedral conformations observed in 1-Zn-D-Phe were herein arbitrarily designated as alpha(1) and alpha(2). DFT calculation suggests that the D-Phe binding prefer the alpha(1)-conformer: the energy of D-Phe-alpha(1) is more stable than L-Phe-alpha(1) by 5.5 kcal/mol. This preference to one diastereomer generates amplification of CD signal with Cotton effect, which can be applied to the determination of ee values of the amino acid.
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