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Chiroptical sensing of amino acids by stereodynamic imprinting into the Zn-II-Complex generating a dihedral chirality
- Title
- Chiroptical sensing of amino acids by stereodynamic imprinting into the Zn-II-Complex generating a dihedral chirality
- Authors
- Chen, Qian; Shirbhate, Mukesh Eknath; Kim, Youngmee; Kim, Sung-Jin; Kang, Baotao; Kim, Kwan Mook
- Ewha Authors
- 김성진; 김영미; 김관묵
- SCOPUS Author ID
- 김성진; 김영미; 김관묵
- Issue Date
- 2019
- Journal Title
- DYES AND PIGMENTS
- ISSN
- 0143-7208
1873-3743
- Citation
- DYES AND PIGMENTS vol. 164, pp. 227 - 232
- Keywords
- Circular dichroism amplification; Absolute configuration of amino acid; Enantiomeric excess determination; Dihedral chirality; Stereodynamic imprinting
- Publisher
- ELSEVIER SCI LTD
- Indexed
- SCIE; SCOPUS
- Document Type
- Article
- Abstract
- 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.
- DOI
- 10.1016/j.dyepig.2019.01.007
- Appears in Collections:
- 자연과학대학 > 화학·나노과학전공 > Journal papers
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