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Conversion of lignin-derived 3-methoxycatechol to the natural product purpurogallin using bacterial P450 GcoAB and laccase CueO.

Purpurogallin is a natural benzotropolone extracted from Quercus spp, which has antioxidant, anticancer, and anti-inflammatory properties. Purpurogallin is typically synthesized from pyrogallol using enzymatic or metal catalysts, neither economically feasible… Click to show full abstract

Purpurogallin is a natural benzotropolone extracted from Quercus spp, which has antioxidant, anticancer, and anti-inflammatory properties. Purpurogallin is typically synthesized from pyrogallol using enzymatic or metal catalysts, neither economically feasible nor environmentally friendly. 3-Methoxycatechol (3-MC) is a lignin-derived renewable chemical with the potential to be a substrate for the biosynthesis of purpurogallin. In this study, we designed a pathway to produce purpurogallin from 3-MC. We first characterized four bacterial laccases and identified the laccase CueO from Escherichia coli, which converts pyrogallol to purpurogallin. Then, we used CueO and the P450 GcoAB reported to convert 3-MC to pyrogallol, to construct a method for producing purpurogallin directly from 3-MC. A total of 0.21 ± 0.05 mM purpurogallin was produced from 5 mM 3-MC by whole-cell conversion. This study provides a new method to enable efficient and sustainable synthesis of purpurogallin and offers new insights into lignin valorization. KEY POINTS: • Screening four bacterial laccases for converting pyrogallol to purpurogallin. • Laccase CueO from Escherichia coli presenting the activity for purpurogallin yield. • A novel pathway for converting lignin-derived 3-methoxycatechol to purpurogallin.

Keywords: purpurogallin; cueo; laccase cueo; lignin derived; p450 gcoab

Journal Title: Applied microbiology and biotechnology
Year Published: 2021

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