2. Academic Validation
  3. Attempt to simultaneously generate three chiral centers in 4-hydroxyisoleucine with microbial carbonyl reductases

Attempt to simultaneously generate three chiral centers in 4-hydroxyisoleucine with microbial carbonyl reductases

  • Bioorg Med Chem. 2018 Apr 1;26(7):1327-1332. doi: 10.1016/j.bmc.2017.06.044.
Makoto Hibi 1,  Koji Takahashi 2,  Junko Kako 3,  Yuuta Wakita 2,  Tomohiro Kodera 4,  Sakayu Shimizu 2,  Kenzo Yokozeki 3,  Jun Ogawa 5
Affiliations

Affiliations

  • 1 Industrial Microbiology, Graduate School of Agriculture, Kyoto University, Kitashirakawa-oiwakecho, Sakyo-ku, Kyoto 606-8502, Japan; Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan.
  • 2 Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Kitashirakawa-oiwakecho, Sakyo-ku, Kyoto 606-8502, Japan.
  • 3 Industrial Microbiology, Graduate School of Agriculture, Kyoto University, Kitashirakawa-oiwakecho, Sakyo-ku, Kyoto 606-8502, Japan.
  • 4 Institute of Food Sciences & Technologies Flavor Innovation Group, Ajinomoto Co, Inc, 1-1, Suzuki-cho, Kawasaki-ku, Kawasaki 210-8681, Japan.
  • 5 Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Kitashirakawa-oiwakecho, Sakyo-ku, Kyoto 606-8502, Japan. Electronic address: ogawa@kais.kyoto-u.ac.jp.
PMID: 28698052 DOI: 10.1016/j.bmc.2017.06.044
Abstract

A panel of Microorganisms was screened for selective reduction ability towards a racemic mixture of prochiral 2-amino-3-methyl-4-ketopentanoate (rac-AMKP). Several of the Microorganisms tested produced greater than 0.5mM 4-hydroxyisoleucine (HIL) from rac-AMKP, and the stereoselectivity of HIL formation was found to depend on the taxonomic category to which the microorganism belonged. The Enzymes responsible for the AMKP-reducing activity, ApAR and FsAR, were identified from two of these Microorganisms, Aureobasidium pullulans NBRC 4466 and Fusarium solani TG-2, respectively. Three AMKP reducing Enzymes, ApAR, FsAR, and the previously reported BtHILDH, were reacted with rac-AMKP, and each enzyme selectively produced a specific composition of HIL stereoisomers. The Enzymes appeared to have different characteristics in recognition of the stereostructure of the substrate AMKP and in control of the 4-hydroxyl group configuration in the HIL product.

Keywords

4-Hydroxyisoleucine; Asymmetric biosynthesis; Carbonyl reductase; Kinetic resolution; Stereoisomer.

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