Prenylation of Flavonoids by Using a Dimethylallyltryptophan Synthase, 7‐DMATS, from Aspergillus fumigatus

Abstract

Production of typical plant metabolites by a fungal enzyme: Fungal prenyltransferases of the DMATS superfamily are mainly involved in the biosynthesis of prenylated indole alkaloids, but also catalyze the prenylation of tyrosine and naphthalene derivatives. In this study, nine prenylated flavonoids were produced by using the recombinant dimethylallyltryptophan synthase 7-DMATS from Aspergillus fumigatus.

Site-directed Mutagenesis Switching a Dimethylallyl Tryptophan Synthase to a Specific Tyrosine C3-Prenylating Enzyme

“…Therefore, the result provides an exciting example for creating biocatalysts by mutation of known enzymes. It is also considerable that enzymes for specific prenylation of flavonoids or hydroxynaphthalenes could be created by mutation of some members of the DMATS superfamily because such compounds have already been accepted by some of these enzymes as prenylation substrates (20,47). Meanwhile, this study presents an excellent example of successful interdisciplinary cooperation and of the importance of structure biology in the discovery and development of novel biocatalysts.…”

Biochemical Characterization of Indole Prenyltransferases

“…Both C5-and C4-or C6-prenylated derivatives were identified in this case (supplemental Table S4). The acceptance of C5-substituted tryptophan derivatives by 5-DMATS could also be explained by the substrate promiscuity of indole prenyltransferases of the DMATS superfamily, which accepted even hydroxynaphthalenes and flavonoids as substrates and catalyzed C-, O-, or both prenylations (46,47).…”

“…2). Therefore, there is a need to find enzymes for C5-prenylation at the indole nucleus, so that these enzymes could be better used as tools for chemoenzymatic synthesis of prenylated indole derivatives or even for synthesis of prenylated hydroxynaphthalenes and flavonoids, which have been very recently described for several members of the DMATS superfamily (46,47).…”

Molecular Characterization and Phylogenetic Analysis of Two Novel Regio-specific Flavonoid Prenyltransferases from Morus alba and Cudrania tricuspidata

“…Moreover, due to their substrate promiscuity in vitro, some soluble types of aromatic PTs from microbes have been demonstrated to be capable of catalyzing the prenylation of flavonoids; e.g. 7-DMATS, a member of DMATS superfamily from Aspergillus fumigatus (18,19), and some PTs of the CloQ/ NphB group from the actinomycetes Streptomyces (20,21).…”