3 years ago

Post Polyketide Synthase Carbon–Carbon Bond Formation in Type-II PKS-Derived Natural Products from Streptomyces venezuelae

Post Polyketide Synthase
Carbon–Carbon Bond
Formation in Type-II PKS-Derived
Natural Products from Streptomyces venezuelae
David L. Jakeman, Leah G. Bennett, Kerry B. Goralski, Hebelin Correa, Andrew W. Robertson, Steven R. Hall, Russell G. Kerr, Jeanna M. MacLeod, Stephanie. M. Forget, Logan W. MacIntyre
Polyketide synthase (PKS) derived natural products are biosynthesized by head-to-tail addition of acetate and malonate extender units resulting in linear extended-polyketide chains. Despite the well-documented structural diversity associated with PKS-derived natural products, C–C chain branching deviating from the usual linear pattern is relatively rare. Herein, type-II PKS angucyclic natural products containing a hemiaminal functionality were identified and proposed as the parent of a series of C–C-branched analogues. These C–C linked acetate or pyruvate branching units were located at the α-positions on the extended polyketide chains of jadomycins incorporating 3- and 4-aminomethylbenzoic acids. Labeling studies utilizing [1-13C]-d-glucose provided mechanistic evidence that the C–C bond formation occurred as a result of a previously unidentified post-PKS processing, additional to the enzymes encoded within the biosynthetic gene cluster. Selected compounds were evaluated in cytotoxic or antimicrobial assays.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02823

DOI: 10.1021/acs.joc.7b02823

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