Novel Enzyme Family Found in Filamentous Fungi Catalyzing trans-4-Hydroxylation of L-Pipecolic Acid

Applied and Environmental Microbiology
Makoto HibiJun Ogawa

Abstract

Hydroxypipecolic acids are bioactive compounds widely distributed in nature and are valuable building blocks for the organic synthesis of pharmaceuticals. We have found a novel hydroxylating enzyme with activity toward L-pipecolic acid (L-Pip) in a filamentous fungus, Fusarium oxysporum c8D. The enzyme L-Pip trans-4-hydroxylase (Pip4H) of F. oxysporum (FoPip4H) belongs to the Fe(II)/α-ketoglutarate-dependent dioxygenase superfamily, catalyzes the regio- and stereoselective hydroxylation of L-Pip, and produces optically pure trans-4-hydroxy-L-pipecolic acid (trans-4-L-HyPip). Amino acid sequence analysis revealed several fungal enzymes homologous with FoPip4H, and five of these also had L-Pip trans-4-hydroxylation activity. In particular, the homologous Pip4H enzyme derived from Aspergillus nidulans FGSC A4 (AnPip4H) had a broader substrate specificity spectrum than other homologues and reacted with the L and D forms of various cyclic and aliphatic amino acids. Using FoPip4H as a biocatalyst, a system for the preparative-scale production of chiral trans-4-L-HyPip was successfully developed. Thus, we report a fungal family of L-Pip hydroxylases and the enzymatic preparation of trans-4-L-HyPip, a bioactive compound and a constitue...Continue Reading

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Citations

May 11, 2017·Chembiochem : a European Journal of Chemical Biology·Johanna Mattay, Wolfgang Hüttel
Jan 21, 2018·Applied and Environmental Microbiology·Johanna MattayWolfgang Hüttel
Oct 6, 2016·Zeitschrift Für Naturforschung. C, a Journal of Biosciences·Wolfgang Hüttel
Jul 24, 2018·The Plant Journal : for Cell and Molecular Biology·Michael Hartmann, Jürgen Zeier
Jul 11, 2018·Applied Microbiology and Biotechnology·Feng ZhangXiangfeng Meng
Apr 16, 2020·Applied Microbiology and Biotechnology·Ryotaro Hara, Kuniki Kino
Dec 24, 2019·Chemical Reviews·Jason B Hedges, Katherine S Ryan

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