Chiroptical sensing of amino acids by stereodynamic imprinting into the Zn II -Complex generating a dihedral chirality

Qian Chen, Mukesh Eknath Shirbhate, Youngmee Kim, Sung Jin Kim, Baotao Kang, Kwan Mook Kim

Research output: Contribution to journalArticlepeer-review

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 Zn II 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 α 1 and α 2 . DFT calculation suggests that the D-Phe binding prefer the α 1 -conformer: the energy of D-Phe-α 1 is more stable than L-Phe-α 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.

Original languageEnglish
Pages (from-to)227-232
Number of pages6
JournalDyes and Pigments
Volume164
DOIs
StatePublished - May 2019

Keywords

  • Absolute configuration of amino acid
  • Circular dichroism amplification
  • Dihedral chirality
  • Enantiomeric excess determination
  • Stereodynamic imprinting

Fingerprint

Dive into the research topics of 'Chiroptical sensing of amino acids by stereodynamic imprinting into the Zn II -Complex generating a dihedral chirality'. Together they form a unique fingerprint.

Cite this