Kinetic resolution of chiral amines using packed-bed reactor

Jong Shik Shin, Byung Gee Kim, Dong Hoon Shin

Research output: Contribution to journalArticle

46 Citations (Scopus)

Abstract

A kinetic resolution process for production of chiral amines is developed using entrapped whole cells of Vibrio fluvialis JS17 in 2% (w/v) Ca-alginate gel beads. External diffusion limitation does not appear to affect reaction rate, and the loss of enzyme activity of the entrapped whole cells would be mainly due to internal diffusion limitation. Stability of the entrapped whole cells is greatly dependent on pH, and the stability is best at pH 8 although the optimal pH for the enzyme activity is 9. The entrapped whole cells showed lower substrate inhibition by (S)-α-methylbenzylamine ((S)-α-MBA) and lower product inhibition by acetophenone than the free cells, whereas the reverse trends were observed for the inhibitions by pyruvate and L-alanine. The results can be explained by partitioning behavior of the compounds between bulk aqueous phase and gel beads. Kinetic resolutions of α-MBA, 1-aminotetralin, and 1-aminoindan were performed using a packed-bed reactor (PBR) packed with the entrapped whole cells and a hydrophobic membrane contactor to continuously remove inhibitory ketone. Considering different degree of substrate inhibitions by the racemic amines, feed method was varied carefully. The reaction profiles indicate that use of low concentration of the amine substrate and repetitive batch reaction rather than fed-batch reaction is preferable due to the substrate inhibition by slow-reacting (R)-amine as well as by (S)-amine.

Original languageEnglish
Pages (from-to)232-239
Number of pages8
JournalEnzyme and Microbial Technology
Volume29
Issue number4-5
DOIs
Publication statusPublished - 2001 Sep 5

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Packed beds
Amines
Kinetics
Enzyme activity
Substrates
Gels
Alginate
Ketones
Pyruvic Acid
Vibrio
Alanine
Reaction rates
Enzymes
Membranes

All Science Journal Classification (ASJC) codes

  • Biotechnology
  • Bioengineering
  • Biochemistry
  • Applied Microbiology and Biotechnology

Cite this

Shin, Jong Shik ; Kim, Byung Gee ; Shin, Dong Hoon. / Kinetic resolution of chiral amines using packed-bed reactor. In: Enzyme and Microbial Technology. 2001 ; Vol. 29, No. 4-5. pp. 232-239.
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Kinetic resolution of chiral amines using packed-bed reactor. / Shin, Jong Shik; Kim, Byung Gee; Shin, Dong Hoon.

In: Enzyme and Microbial Technology, Vol. 29, No. 4-5, 05.09.2001, p. 232-239.

Research output: Contribution to journalArticle

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