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Volume 19, Issue 3, Pages 422-432 (March 2012) Unveiling the Post-PKS Redox Tailoring Steps in Biosynthesis of the Type II Polyketide Antitumor Antibiotic Xantholipin Weike Zhang, Lu Wang, Lingxin Kong, Tao Wang, Yiwen Chu, Zixin Deng, Delin You Chemistry & Biology Volume 19, Issue 3, Pages 422-432 (March 2012) DOI: 10.1016/j.chembiol.2012.01.016 Copyright © 2012 Elsevier Ltd Terms and Conditions

Chemistry & Biology 2012 19, 422-432DOI: (10. 1016/j. chembiol. 2012 Copyright © 2012 Elsevier Ltd Terms and Conditions

Figure 1 Structures of Xantholipin and Derivatives Orange, xanthone; blue, cyclic amide. Chemistry & Biology 2012 19, 422-432DOI: (10.1016/j.chembiol.2012.01.016) Copyright © 2012 Elsevier Ltd Terms and Conditions

Figure 2 The Organization of the Xantholipin Biosynthetic Gene Cluster The gene cluster spans 52 kb and contains 49 ORFs. Genes are organized according to their proposed roles (see also Table 1); the underlined genes were individually inactivated, except for orf1–5, orf6–9, and xanY3–Y5, which were deleted together. The 40 kb gray part of fosmid 28B8 is the region that was deleted in strain ZWK1. The construction and verification of the deletion mutants are shown in Figure S1. Chemistry & Biology 2012 19, 422-432DOI: (10.1016/j.chembiol.2012.01.016) Copyright © 2012 Elsevier Ltd Terms and Conditions

Figure 3 Proposed Xantholipin Biosynthetic Pathway Black underline, structure confirmed using NMR or X-ray crystallography as shown in Figure S2; black triangle, gene deleted in producer strain; shading, latest chemical change. See also Figure S6. Chemistry & Biology 2012 19, 422-432DOI: (10.1016/j.chembiol.2012.01.016) Copyright © 2012 Elsevier Ltd Terms and Conditions

Figure 4 Analysis of Antibiotic Production by S. Flavogriseus and Its Mutant Derivatives Top, UV spectra of compounds 1 (xantholipin, yellow), 6 (red), and 8a (yellow). Bottom, HPLC traces (274 nm UV absorption). The formulas of the compounds were given by Q-TOF Mass shown in Figure S3. Note, 8b was generated during the crystallization from methanol for X-ray analysis. See also Figure S5. Chemistry & Biology 2012 19, 422-432DOI: (10.1016/j.chembiol.2012.01.016) Copyright © 2012 Elsevier Ltd Terms and Conditions

Figure 5 Phylogenetic Analysis of the XanZ3, XanZ4, and Their Homologs PDB ID codes: LlpZI, CAM34340; GrhO10, AAM33668; RubG, AAG03071; BenL, CAM58804; FdmO, AAQ08926; SanO, ADG86325; PnxG, BAJ52686; LlpZIII, CAM34370; PnxW, BAJ52708; ChaL, CAH10174; AknU, AF264025; DnrH, AAA65202; FabG, EGT67884. See also Figure S4. Chemistry & Biology 2012 19, 422-432DOI: (10.1016/j.chembiol.2012.01.016) Copyright © 2012 Elsevier Ltd Terms and Conditions