Enantio- and chemoselective differentiation of protected α-amino acids and β-homoamino acids with a single copper(II) host

Leo A. Joyce, James W. Canary, Eric V. Anslyn

Research output: Contribution to journalArticle

Abstract

The association between an achiral copper(II)-containing host 1 and chiral carboxylates has been expanded beyond previous studies to new chiral carboxylate guests, both α-amino acids and β-homoamino acids. The observed exciton-coupled circular dichroism (ECCD) signals for the enantiomers of each carboxylate were equal and opposite, and these signals differed in size and shape between the individual amino acids. Linear discriminant analysis (LDA) was applied as a statistical analysis technique to differentiate the amino acids, both enantioselectively and chemoselectively, giving the absolute configuration and identity of the amino acid. The identity of each of the α-amino acids and β-homoamino acids were determined independently by LDA, and then the two were considered together. Each of these analyses showed good differentiation of the amino acid guests with the use of only one host molecule.

Original languageEnglish (US)
Pages (from-to)8064-8069
Number of pages6
JournalChemistry - A European Journal
Volume18
Issue number26
DOIs
StatePublished - Jun 25 2012

    Fingerprint

Keywords

  • amino acids
  • chemoselectivity
  • chirality
  • circular dichroism
  • enantioselectivity

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

Cite this