Immobilization of Phenylalanine Ammonia-Lyase on Single-Walled Carbon Nanotubes for Stereoselective Biotransformations in Batch and Continuous-Flow Modes

Judith H. Bartha-Vári, Monica I. Toşa, Florin Dan Irimie, Diána Weiser, Zoltán Boros, Beáta G. Vértessy, Csaba Paizs, László Poppe

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

Carboxylated single-walled carbon nanotubes (SwCNTCOOH) were used as a support for the covalent immobilization of phenylalanine ammonia-lyase (PAL) from parsley by two different methods. The nanostructured biocatalysts (SwCNTCOOH-PALI and SwCNTCOOH-PALII) with low diffusional limitation were tested in the batch-mode kinetic resolution of racemic 2-amino-3-(thiophen-2-yl)propanoic acid (1) to yield a mixture of (R)-1 and (E)-3-(thiophen-2-yl)acrylic acid (2) and in ammonia addition to 2 to yield enantiopure (S)-1. SwCNTCOOH-PALII was a stable biocatalyst (> 90 % of the original activity remained after six cycles with 1 and after three cycles in 6 M NH3 with 2). The study of ammonia addition to 2 in a continuous-flow microreactor filled with SwCNTCOOH-PALII (2 M NH3, pH 10.0, 15 bar) between 30-80°C indicated no significant loss of activity over 72 h up to 60°C. SwCNTCOOH-PALII in the continuous-flow system at 30°C was more productive (specific reaction rate, rflow = 2.39 μmol m-1 g-1) than in the batch reaction (rbatch = 1.34 μmolmin-1 g-1).

Original languageEnglish
Pages (from-to)1122-1128
Number of pages7
JournalChemCatChem
Volume7
Issue number7
DOIs
Publication statusPublished - Apr 7 2015

Keywords

  • biotransformations
  • enzyme catalysis
  • immobilization
  • nanotubes
  • supported catalysts

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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