Biosynthesis and applications of prenylquinones

Abstract

Prenylquinones are isoprenoid compounds with a characteristic quinone structure and isoprenyl tail that are ubiquitous in almost all living organisms. There are four major prenylquinone classes: ubiquinone (UQ), menaquinone (MK), plastoquinone (PQ), and rhodoquinone (RQ). The quinone structure and isoprenyl tail length differ among organisms. UQ, PQ, and RQ contain benzoquinone, while MK contains naphthoquinone. UQ, MK, and RQ are involved in oxidative phosphorylation, while PQ functions in photosynthetic electron transfer. Some organisms possess two types of prenylquinones; Escherichia coli has UQ₈ and MK₈, and Caenorhabditis elegans has UQ₉ and RQ₉. Crystal structures of most of the enzymes involved in MK synthesis have been solved. Studies on the biosynthesis and functions of quinones have advanced recently, including for phylloquinone (PhQ), which has a phytyl moiety instead of an isoprenyl tail. Herein, the synthesis and applications of prenylquinones are reviewed.

Keywords: DHFL: dehypoxanthinylfutalosine; DHNA: 1,4-dihydroxy-2-naphthoate; DMAPP: dimethylallyl pyrophosphate; DMK: demethylmenaquinone; DXP: 1-deoxy-D-xylulose-5-phosphate; FPP: farnesyl pyrophosphate; GGPP: geranylgeranyl pyrophosphate; GPP: geranyl pyrophosphate; HGA: homogentisate; IPP: isopentenyl pyrophosphate; MEP: 2C-methyl-D-erythritol-4-phosphate; MK: menaquinone; MVA: mevalonate; PDS: prenyl diphosphate synthase; PHB: p-hydroxybenzoate; PQ: plastoquinone; PhQ: phylloquinone; RQ: rhodoquinone; UQ: ubiquinone; Ubiquinone; menaquinone; phylloquinone; plastoquinone; rhodoquinone.