Discrimination of the Chirality of α-Amino Acids in ZnII Complexes of DPA-Appended Binaphthyl Imine

Mukesh Eknath Shirbhate, Raju Nandhakumar, Youngmee Kim, Sung Jin Kim, Seong Kyu Kim, Kwan Mook Kim

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

Binaphthol aldehydes with appended dipicolylamine moieties, (R)-1, and (R)-2, were synthesized. The reaction of (R)-1 with an amino acid together with the ZnII ion produces a monomeric complex that discriminates the chirality of the bound amino acid by 1H NMR spectroscopy. The same reaction of (R)-2, which is different from (R)-1 by only one nitrogen atom, generates a dimeric complex that is highly enantiospecific for the l-form of amino acids such as Phe and Trp.

Original languageEnglish
Pages (from-to)4959-4964
Number of pages6
JournalEuropean Journal of Organic Chemistry
Volume2018
Issue number35
DOIs
StatePublished - 23 Sep 2018

Keywords

  • Amino acids
  • Chirality
  • Enantioselectivity
  • Zinc

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