Marinone
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Marinone
Marinone is an antibiotic made by marine actinomycetes. Biosynthesis The proposed biosynthesis of marinone was first reported by Murray ''et al.'' in 2018. The biosynthesis of marinone begins with 1,3,6,8-tetrahydroxynaphthalene (THN), which is known to be biosynthesized via the condensation of five malonyl-coenzyme A units followed by the aromatization of the resulting pentaketide using a type III polyketide synthase. Next, THN undergoes geranylation or farnesylation Prenylation (also known as isoprenylation or lipidation) is the addition of hydrophobic molecules to a protein or a biomolecule. It is usually assumed that prenyl groups (3-methylbut-2-en-1-yl) facilitate attachment to cell membranes, similar to ... at the C-4 position, yielding 1 (Fig. 1). This transformation is catalyzed in vivo by NphB aromatic prenyltransferase in naphterpin biosynthesis or by CnqP3 or CnqP4 in marinone biosynthesis. Then, 1 undergoes oxidative dearomatization which is catalyzed by VCPO, ...
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Debromomarinone
Debromomarinone is a chemical compound isolated from marine actinomycetes. Biosynthesis The proposed biosynthesis of marinone was first reported by Murray ''et al.'' in 2018. The biosynthesis of marinone begins with 1,3,6,8-tetrahydroxynaphthalene (THN), which is known to be biosynthesized via the condensation of five malonyl-coenzyme A units followed by the aromatization of the resulting pentaketide using a type III polyketide synthase. Next, THN undergoes geranylation or farnesylation at the C-4 position, yielding 1 (Fig. 1). This transformation is catalyzed in vivo by NphB aromatic prenyltransferase in naphterpin biosynthesis or by CnqP3 or CnqP4 in marinone biosynthesis. Then, 1 undergoes oxidative dearomatization which is catalyzed by VCPO, which is a vanadium-dependent chloroperoxidase enzyme. This transformation yields compound 2. Compound 2 then undergoes two consecutive chlorinations at the C2 position, catalyzed by VCPO, to yield 4. Next, a VCPO catalyzed α-hydroxyketo ...
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