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Biomolecules 2016, 6(4), 41; doi:10.3390/biom6040041

Continuous Reusability using Immobilized HasApf in Chemoenzymatic Deracemization: A New Heterogeneous Enzyme Catalysis

Sanyo Shokuhin Co., Ltd. R & D, 555-4 Asakura, Maebashi, Gunma 371-0811, Japan
Academic Editor: Emily Weinert
Received: 5 August 2016 / Revised: 30 September 2016 / Accepted: 14 October 2016 / Published: 25 October 2016
(This article belongs to the Special Issue Advances in Heme Proteins)
View Full-Text   |   Download PDF [1964 KB, uploaded 25 October 2016]   |  

Abstract

This study found that the calibration curve of heme acquisition system A (HasA, a new reactive active species) immobilized by a porous ceramic particle (ImHApf; immobilized HasA from Pseudomonas fluorescens) can be constructed in the range of 1750–1450 cm−1 using Fourier transform infrared spectroscopy (FTIR) analysis, and evaluated its catalytic efficiency. In the asymmetric oxidation of rac-1-(6-methoxynaphthalen-2-yl)ethanol (rac-1: a naproxen precursor), a product ketone from the (R)-isomer is desymmetrized using NaBH4 and continuously reused even if treated with an organic solvent in 50 mM glycine–NaOH buffer at 40 °C in the absence of nicotinamide adenine dinucleotide (NAD(P)), leading to >99% enantiomeric excess and >90% chemical yield; the activity was calculated at 0.74 ± 0.03 mU/(mg·min) and the turnover number was determined to be approximately 2 × 106. It was confirmed that the other sec-alcohols such as rac-1-(2-naphthyl)ethanol (rac-2) and m- and p-substituted rac-1-phenyl ethanols (rac-3ab6ab) using ImHApf can also yield a single stereoisomer from a racemate. Therefore, HasA immobilization can be expected to become an important tool for building an environmentally friendly system that promotes industrial sustainability. View Full-Text
Keywords: immobilized HasA; iron electron-transfer system; porous ceramic particle; continuous reusability; chemoenzymatic deracemization immobilized HasA; iron electron-transfer system; porous ceramic particle; continuous reusability; chemoenzymatic deracemization
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Nagaoka, H. Continuous Reusability using Immobilized HasApf in Chemoenzymatic Deracemization: A New Heterogeneous Enzyme Catalysis. Biomolecules 2016, 6, 41.

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