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The majority of modular polyketide synthase (PKS) systems which generate unsaturated products do so with trans double bonds. Phoslactomycin B (PLM B) presents a class of antitumor and antiviral natural polyketide products that have unique structural features, including a linear unsaturated backbone with one trans and three cis double bonds. There is substantial evidence that trans double bonds are established by ketoreductase−dehydratase (KR−DH) didomains within a PKS module. In cases where modules containing these didomains appear to generate product containing a cis double bond, there is no experimental evidence to determine if they do so directly or if they also form a trans double bond with a subsequent isomerization step. A critical step in addressing this issue is establishing the stereochemistry of the polyketide intermediate which passes to the subsequent module. Herein, we demonstrate through a series of experiments that an activated cis-3-cyclohexylpropenoic acid is the diketide intermediate whi...

journal of the american chemical society

Modular Polyketide Synthases and <i>cis</i> Double Bond Formation: Establishment of Activated <i>cis</i>-3-Cyclohexylpropenoic Acid as the Diketide Intermediate in Phoslactomycin Biosynthesis

Modular Polyketide Synthases and cis Double Bond Formation: Establishment of Activated cis-3-Cyclohexylpropenoic Acid as the Diketide Intermediate in Phoslactomycin Biosynthesis