Biosynthetic pathway of coenzyme Q8 in E. coli. The numbering of the aromatic carbon atoms used throughout this study is shown on Q8, and the octaprenyl tail is represented by R on carbon 3 of the different biosynthetic intermediates. The name of the enzymes catalyzing the reactions (each labeled with a lowercase letter) is indicated. The enzyme catalyzing the C5-hydroxylation (reaction c) is unknown (see full text for further details). Abbreviations for coenzyme Q8 (Q8), C6-demethoxy-Q8 (DMQ8), C1-demethyl-C6-demethoxy-Q8 (DDMQ8), 3-octaprenyl-4-hydroxybenzoic acid (OHB), and 3-octaprenylphenol (OPP) are underlined.