Natural products with one or more prenyl groups have been isolated to date mainly from higher plants. These compounds originating from multiple natural product classes often possess anti-microbial, anti-oxidant, anti-inflammatory, anti-viral and anti-cancer activities. However, prenylated compounds are found at trace levels in natural sources and are not often amenable to synthesis in a cost effect manner. Given the recent identification of catalytically promiscuous prenyltransferases displaying regiospecificity in prenyl group transfer and prenyl chain selectivity, these biocatalysts can serve as an alternate production strategy. NphB is a soluble prenyltransferase from Streptomyces sp. strain CL190 that attaches a geranyl group to a 1,3,6,8-tetrahydroxynaphthalene-derived naphthoquinone during the biosynthesis of anti-oxidant naphterpin. In the present paper, I introduce multiple chemoenzymatic syntheses of various prenylated compounds from aromatic substrates including flavonoids and phenylpropanoids using three Streptomyces prenyltransferases NphB [1,2], Fur7 [3] and NovQ [4] as biocatalysts.
References.
1) Kuzuyama, T., et al. 2005. Structural basis for the promiscuous biosynthetic prenylation of aromatic natural products. Nature 435: 983-987.
2) Kumano T., et al. 2008. Chemoenzymatic syntheses of prenylated aromatic small molecules using Streptomyces prenyltransferases with relaxed substrate specificities. Bioorg. Med. Chem. 16: 8117-8126.
3) Kawasaki, T., et al. 2006. Biosynthesis of a natural polyketide-isoprenoid hybrid compound furaquinocin A: Identification and heterologous expression of the gene cluster. J. Bacteriol. 188: 1236-1244.
4) Ozaki, T., et al. 2009. NovQ is a prenyltransferase capable of catalyzing the addition of a dimethylallyl group to both phenylpropanoids and flavonoids. J. Antibiot. 62: 385-392.
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