Immobilization of phenylalanine ammonia-lyase on single-walled carbon nanotubes for stereoselective biotransformations in batch and in continuous-flow modes

Bartha-Vári, Judith H. and Toşa, Monica I. and Irimie, Florin-Dan and Weiser, Diána and Boros, Zoltán and Vértessy, Beáta (Grolmuszné) and Poppe, László (2015) Immobilization of phenylalanine ammonia-lyase on single-walled carbon nanotubes for stereoselective biotransformations in batch and in continuous-flow modes. CHEMCATCHEM, 7 (7). pp. 1122-1128. ISSN 1867-3880

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Abstract

Carboxylated single-walled carbon nanotubes (SwCNTCOOH) were used as support for 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 batch mode kinetic resolution of racemic 2-amino-3-(thiophen-2-yl)propanoic acid 1 [yielding a mixture of (R)-1 and (E)-3-(thiophen-2-yl)acrylic acid 2] and in the ammonia addition onto 2 [yielding enantiopure (S)-1]. SwCNTCOOH-PALII was a stable biocatalyst (>90% of original activity after 6 cycles with 1 and after 3 cycles in 6 M NH3 with 2). Study of NH3 addition to 2 in 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 (rflow=2.39 mol min-1 g-1) than in the batch reaction (rbatch= 1.34 mol min-1 g-1).

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