Lignin Peroxidase-Catalyzed Selective Cleavage of C–C Bonds in Lignin at Room Temperature
Trang Vu Thien Nguyen, Saerona Kim, Chang Geun Yoo, Joon Weon Choi, Gyu Leem, Yong Hwan Kim
Abstract
High Resolution Image Download MS PowerPoint Slide Selective oxidative cleavage of C–C linkages is a challenge for chemical transformations including lignin depolymerization. This study reports recombinant Phanerochaete chrysosporium lignin peroxidase isozyme 1 (PcLiP01)-catalyzed nonpolar C–C σ-bond cleavage in lignin model compounds (LMCs), dehydrogenative polymer (DHP), and real milled wood lignin (MWL) to produce a targeted value-added aromatic compound, 2,6-dimethoxy-1,4-benzoquinone (DMBQ) under mild conditions. Notably, according to pH-dependent redox reactions with both phenolic and nonphenolic LMCs, C aryl –C α cleavage products of the LMCs were dominant under low pH ∼ 3 compared to pH ∼ 5. Furthermore, the oxidative conversion of DHP and MWL using PcLiP01 showed 12 and 5 mg/g substrate yields of DMBQ, respectively. These findings offer an approach to support a C–C bond cleavage reaction with less-reactive nonphenolic LMCs and provide valuable insights into the oxidative conversion of lignin to the value-added chemical DMBQ with PcLiP01.