Water-Soluble Anthraquinone Photocatalysts Enable Methanol-Driven Enzymatic Halogenation and Hydroxylation Reactions

Bo Yuan; Durga Mahor; Qiang Fei; Ron Wever; Miguel Alcalde; Wuyuan Zhang; Frank Hollmann

doi:10.1021/acscatal.0c01958

Water-Soluble Anthraquinone Photocatalysts Enable Methanol-Driven Enzymatic Halogenation and Hydroxylation Reactions

ACS Catal. 2020 Aug 7;10(15):8277-8284. doi: 10.1021/acscatal.0c01958. Epub 2020 Jun 30.

Authors

Bo Yuan¹, Durga Mahor¹, Qiang Fei¹, Ron Wever², Miguel Alcalde³, Wuyuan Zhang¹, Frank Hollmann⁴

Affiliations

¹ School of Chemical Engineering and Technology, Xi'an Jiaotong University, Xi'an 710049, China.
² Van't Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, 1098 XH Amsterdam, The Netherlands.
³ Department of Biocatalysis, Institute of Catalysis, CSIC, 28049 Madrid, Spain.
⁴ Department of Biotechnology, Delft University of Technology, Van der Maasweg 9, 2629HZ Delft, The Netherlands.

Abstract

Peroxyzymes simply use H₂O₂ as a cosubstrate to oxidize a broad range of inert C-H bonds. The lability of many peroxyzymes against H₂O₂ can be addressed by a controlled supply of H₂O₂, ideally in situ. Here, we report a simple, robust, and water-soluble anthraquinone sulfonate (SAS) as a promising organophotocatalyst to drive both haloperoxidase-catalyzed halogenation and peroxygenase-catalyzed oxyfunctionalization reactions. Simple alcohols, methanol in particular, can be used both as a cosolvent and an electron donor for H₂O₂ generation. Very promising turnover numbers for the biocatalysts of up to 318 000 have been achieved.