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The structural diversity of type II polyketides is largely generated by tailoring enzymes. In rishirilide biosynthesis by Streptomyces bottropensis, 13C-labeling studies previously implied extraordinary carbon backbone and side-chain rearrangements. In this work, we employ gene deletion experiments and in vitro enzyme studies to identify key biosynthetic intermediates and expose intricate redox tailoring steps for the formation of rishirilides A, B, and D and lupinacidin A. First, the flavin-dependent RslO5 reductively ring-opens the epo
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