Dynamic Kinetic Resolution of Ethyl 1,2,3,4-Tetrahydro-β-carboline-1-carboxylate: Use of Different Hydrolases for Stereocomplementary Processes

Rita Megyesi, Attila Mándi, Tibor Kurtán, Enikő Forró, Ferenc Fülöp

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Both enantiomers of 1,2,3,4-tetrahydro-β-carboline-1-carboxylic acid have been prepared by dynamic kinetic resolution of the corresponding ethyl ester (±)-1. CAL-B-catalysed hydrolysis of (±)-1·HCl in NH4OAc buffer (pH 8.0, 30 °C) provided amino acid (R)-2·HCl with 98 % ee and 90 % yield in 20 min. The hydrolysis with Alcalase in borate buffer (pH 8.0, 30 °C) showed S selectivity and the product (S)-2·HCl was obtained with 60 % ee and 66 % yield in 45 h. The absolute configuration of (S)-2 was determined by TDDFT electronic circular dichroism and optical rotation calculations.

Original languageEnglish
Pages (from-to)4713-4718
Number of pages6
JournalEuropean Journal of Organic Chemistry
Volume2017
Issue number32
DOIs
Publication statusPublished - Sep 1 2017

Keywords

  • Amino acids
  • Dynamic kinetic resolution
  • Enzyme catalysis
  • Hydrolysis
  • Nitrogen heterocycles

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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