Biomimetic Studies Using Artificial Systems. II. Enantioselective Thiolysis of D- or L-α-Amino Acid Ester Salts by Thiol-Bearing Chiral Crown Ethers as an Enzyme Model

Shigeki Sasaki, Motoji Kawasaki, Kenji Koga

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The rates of transacylation were studied between thiol-bearing chiral crown ethers (1—10) and a-amino acid p-nitrophenyl ester salts. Enantioselectivities, kD/kLratios, of 6.5 for valine ester salt, 8.7 for phenylalanine ester salt, and 7.7 for valine ester salt were achieved by 1, 5, and 8, respectively. Saturation phenomena of rate acceleration depending on crown concentration were observed and analysis of these data revealed that the chiral recognition occurs in the step of liberation of p-nitrophenol by intra-complex thiolysis, not in the complex-forming step. A possible mechanism for the enantioselectivity is proposed on the basis of the kinetic data.

Original languageEnglish
Pages (from-to)4247-4266
Number of pages20
JournalChemical and Pharmaceutical Bulletin
Volume33
Issue number10
DOIs
Publication statusPublished - Jan 1 1985
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Drug Discovery

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