In this study, we first establish heterologous expression systems of the unique antimycin-type cyclic depsipeptides: JBIR tri-lactone and neoantimycin tetra-lactone , and engineer their biosyntheses by taking advantage of bioinformatic analyses and evolutionary insights. As a result, we successfully accomplish three manipulations: i ring contraction of neoantimycin from tetra-lactone to tri-lactone , ii ring expansion of JBIR from tri-lactone to tetra-lactone , and iii alkyl chain diversification of JBIR by the incorporation of various alkylmalonyl-CoA extender units, to generate a set of unnatural derivatives in practical yields. Polyketides and non-ribosomal peptide hybrids are an important class of natural products, and include a variety of bioactive compounds, exemplified by the anti-cancer agents, bleomycin, epothilone, and calyculin 1 — 4. They are built up by a complex system composed of polyketide synthases PKSs and non-ribosomal peptide synthetases NRPSs 5 — 7 , which are thiotemplate module enzymes consisting of several catalytic domains. In the PKS system, the ketosynthase KS domain catalyzes decarboxylative Claisen condensation between a starter acyl group and an extender unit thioesterified to an acyl carrier protein ACP via the action of an acyltransferase AT , during a single polyketide extension cycle.
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The regulation and biosynthesis of antimycins
Evolution of natural products, and particularly those resulting from microbial assembly line-like enzymes, such as polyketide PK and nonribosomal peptides NRP , has resulted in a variety of pharmaceutically important and chemically diverse families of molecules. The antimycin-type depsipeptides are one such grouping, with a significant level of diversity and members that have noted activities against key targets governing human cellular apoptosis e. Bcl-xL and GRP Chemical variance originates from ring size, with 9-, , , and membered classes, and we show that such distinctions influence their molecular targeting. Further, we present here a systematic interrogation of the chemistry and assembly line evolution of antimycin-type analogues by conducting metabolomic profiling and biosynthetic gene cluster comparative analysis of the depsipeptide assembly lines for each member of the antimycin-group. Natural molecular evolution principles of such studies should assist in artificial re-combinatorializing of PK and NRP assembly lines.
Chemical and Biosynthetic Evolution of the Antimycin-Type Depsipeptides
This article is part of the Thematic Series "Natural products in synthesis and biosynthesis". Guest Editor: J. Dickschat Beilstein J. Antimycin A is widely used as a piscicide in the catfish farming industry and also has potent killing activity against insects, nematodes and fungi.