Biosynthesis of the Antitumor Agent Chartreusin Involves the Oxidative Rearrangement of an Anthracyclic Polyketide Zhongli Xu, Kathrin Jakobi, Katrin.

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Presentation transcript:

Biosynthesis of the Antitumor Agent Chartreusin Involves the Oxidative Rearrangement of an Anthracyclic Polyketide Zhongli Xu, Kathrin Jakobi, Katrin Welzel, Christian Hertweck Chemistry & Biology Volume 12, Issue 5, Pages 579-588 (May 2005) DOI: 10.1016/j.chembiol.2005.04.017 Copyright © 2005 Elsevier Ltd Terms and Conditions

Figure 1 Structures of the Potent Antitumor Agents Chartreusin, Elsamicin, and IST-622, and Acetate Labeling Pattern of the Aglycone Charartin Chemistry & Biology 2005 12, 579-588DOI: (10.1016/j.chembiol.2005.04.017) Copyright © 2005 Elsevier Ltd Terms and Conditions

Figure 2 Detection of Chartreusin in Wild-Type and Recombinant Strains (A) HPLC profiles of crude extracts from (a) wild-type S. chartreusis, (b) S. albus/pSC5P21, and (c) host S. albus. (B and C) MSn analyses (in positive [B] and negative [C] modes) of chartreusin (1) produced by S. albus/pSC5P21. Chemistry & Biology 2005 12, 579-588DOI: (10.1016/j.chembiol.2005.04.017) Copyright © 2005 Elsevier Ltd Terms and Conditions

Figure 3 Organization of the cha Biosynthesis Gene Cluster in S. chartreusis Each arrow indicates the direction of transcription and the relative sizes of the ORFs deduced from analysis of the nucleotide sequence. Black ORFs, minimal PKS and cyclase/aromatase genes; light-gray ORFs, ketoreductase genes; dark-gray ORFs, oxidoreductase and methyl transferase genes; checked ORFs, probable regulatory and resistance genes; hatched ORFs, genes putatively involved in deoxysugar biosynthesis and attachment; white ORFs, genes of unknown function. Chemistry & Biology 2005 12, 579-588DOI: (10.1016/j.chembiol.2005.04.017) Copyright © 2005 Elsevier Ltd Terms and Conditions

Figure 4 Proposed Pathway for the Biosynthesis of the 6-Deoxysugars in Chartreusin Chemistry & Biology 2005 12, 579-588DOI: (10.1016/j.chembiol.2005.04.017) Copyright © 2005 Elsevier Ltd Terms and Conditions

Figure 5 Revised Biosynthetic Model for the Chartreusin Aglycone, Chartarin The linear polyketide metabolite resomycin C (8) was isolated from the chaZ null mutant. The previously proposed pathway via benzopyrene 11 is shown for comparison. Chemistry & Biology 2005 12, 579-588DOI: (10.1016/j.chembiol.2005.04.017) Copyright © 2005 Elsevier Ltd Terms and Conditions