Volume 15, Issue 10, Pages (October 2008)

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Volume 15, Issue 10, Pages 1046-1057 (October 2008) Characterization of the Alnumycin Gene Cluster Reveals Unusual Gene Products for Pyran Ring Formation and Dioxan Biosynthesis Terhi Oja, Kaisa Palmu, Hanna Lehmussola, Outi Leppäranta, Kati Hännikäinen, Jarmo Niemi, Pekka Mäntsälä, Mikko Metsä-Ketelä Chemistry & Biology Volume 15, Issue 10, Pages 1046-1057 (October 2008) DOI: 10.1016/j.chembiol.2008.07.022 Copyright © 2008 Elsevier Ltd Terms and Conditions

Figure 1 Structures and Carbon Numbering Alnumycin (1); the BIQ metabolites actinorhodin (2), medermycin (3), granaticin (4), and frenolicin (5); prealnumycin (6); K1115 A (7); and 3,8-dihydroxy-1-methylanthraquinone-2-carboxylic acid (DMAC; 8). Chemistry & Biology 2008 15, 1046-1057DOI: (10.1016/j.chembiol.2008.07.022) Copyright © 2008 Elsevier Ltd Terms and Conditions

Figure 2 Monitoring of Metabolites Produced by Wild-Type and Recombinant Strains HPLC-UV-Vis profiles at 298 nm of crude extracts from (A) wild-type Streptomyces sp. CM020, (B) S. albus/pAlnuori, (C) S. albus/pAoriΔaln4, (D) S. albus/pAoriΔaln5, (E) S. albus/pAoriΔind, and (F) S. albus. Results from LC-MS analysis in positive mode are also shown for (A) and (B). Chemistry & Biology 2008 15, 1046-1057DOI: (10.1016/j.chembiol.2008.07.022) Copyright © 2008 Elsevier Ltd Terms and Conditions

Figure 3 Organization of the aln Biosynthetic Gene Cluster PKS genes responsible for polyketide carbon skeleton synthesis are marked in black; genes responsible for post-PKS tailoring reactions are white; genes of unknown function are dark gray; and genes involved in regulation/resistance are light gray. Chemistry & Biology 2008 15, 1046-1057DOI: (10.1016/j.chembiol.2008.07.022) Copyright © 2008 Elsevier Ltd Terms and Conditions

Figure 4 Model for Alnumycin Biosynthesis The carbon numbering shown is calculated beginning from the enzyme-bound carbon of the formed polyketide chain and differs from the carbon numbering of the end product alnumycin. Chemistry & Biology 2008 15, 1046-1057DOI: (10.1016/j.chembiol.2008.07.022) Copyright © 2008 Elsevier Ltd Terms and Conditions

Figure 5 Comparison of Reactions Involved in Pyran Ring Formation in Actinorhodin, Granaticin, and Alnumycin Biosynthesis R1 = −CH3 and R2 = −CH2CH2CH3. Multiple arrows indicate several biosynthetic steps. Chemistry & Biology 2008 15, 1046-1057DOI: (10.1016/j.chembiol.2008.07.022) Copyright © 2008 Elsevier Ltd Terms and Conditions