Determination of absolute configurations of amino acids by asymmetric autocatalysis of 2-alkynylpyrimidyl alkanol as a chiral sensor

Itaru Sato, Yasushi Ohgo, Hirotaka Igarashi, Daisuke Nishiyama, Tsuneomi Kawasaki, Kenso Soai

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)

Abstract

Asymmetric autocatalysis of 2-alkynyl-5-pyrimidyl alkanol is employed as a chiral sensor of 20 amino acids. Asymmetric autocatalysis using amino acids as chiral initiators gave pyrimidyl alkanols of the absolute configurations that were correlated with those of the amino acids. The enantiomeric excesses of pyrimidyl alkanol are invariably high even when the enantiomeric excess of amino acids is as low as 0.1%. Thus, by determining the absolute configuration of pyrimidyl alkanol with high enantiomeric excess, one can determine the absolute configuration of amino acids even when their enantiomeric excess is low.

Original languageEnglish
Pages (from-to)1783-1787
Number of pages5
JournalJournal of Organometallic Chemistry
Volume692
Issue number9
DOIs
Publication statusPublished - 2007 Apr 1

Keywords

  • Amino acid
  • Asymmetric autocatalysis
  • Chiral initiator
  • Chiral sensor
  • Origin of chirality
  • Pyrimidyl alkanol

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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