Discovery of a Fungal Multicopper Oxidase That Catalyzes the Regioselective Coupling of a Tricyclic Naphthopyranone To Produce Atropisomers

Angewandte Chemie
Mio KawaguchiHiroshi Tomoda

Abstract

Atropisomeric dinapinones A1 and A2 (DPA1 and DPA2) were isolated from a culture of Talaromyces pinophilus FKI-3864. Monapinone coupling enzyme (MCE), which dimerizes naphthopyranone monapinone A (MPA), was purified from a cell-free extract of T. pinophilus FKI-3864. MCE regioselectively dimerizes MPA at the 8,8'-positions to synthesize the atropisomers DPA1 and DPA2 in a ratio of approximately 1:2.5 without a cofactor. The optimal pH value and temperature for MCE were 4.0 and 50 °C, and the apparent Km and Vmax values for MPA were (72.7±23.2) μm and (1.21±0.170) μmol min-1  mg-1  protein. The MCE polypeptide is significantly homologous with multicopper oxidases. Heterologous expression of MCE and functional analysis confirmed that MCE catalyzes the regioselective coupling reaction of MPA to produce DPA. No fungal multicopper oxidase has previously been reported to catalyze regioselective intermolecular oxidative phenol coupling to produce naphthopyranone atropisomers.

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Citations

Feb 13, 2019·Chemical Science·Zhen Zhen ZhouRen Xiang Tan
May 31, 2018·Proceedings of the National Academy of Sciences of the United States of America·Ronnie de JongeMelvin D Bolton
May 3, 2019·Angewandte Chemie·Sebastian ObermaierMichael Müller
Mar 15, 2019·Chembiochem : a European Journal of Chemical Biology·Leon FürtgesMichael Müller
Mar 12, 2020·Chembiochem : a European Journal of Chemical Biology·Wiebke ThieleMichael Müller
Jul 16, 2019·Fungal biology and biotechnology·Andrew S UrquhartAlexander Idnurm
Jul 30, 2019·Magnetic Resonance in Chemistry : MRC·Xiao-Wei LuoYong-Hong Liu
Nov 17, 2020·Natural Product Reports·Wolfgang Hüttel, Michael Müller
Jan 7, 2021·Natural Product Reports·Jiawang LiuYoucai Hu
May 9, 2019·Biochemistry·Sebastian Obermaier, Michael Müller

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