Volume 12, Issue 12, Pages (December 2005)

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Volume 12, Issue 12, Pages 1301-1309 (December 2005) An Iterative Type I Polyketide Synthase PKSN Catalyzes Synthesis of the Decaketide Alternapyrone with Regio-Specific Octa-Methylation Isao Fujii, Naho Yoshida, Shigeki Shimomaki, Hideaki Oikawa, Yutaka Ebizuka Chemistry & Biology Volume 12, Issue 12, Pages 1301-1309 (December 2005) DOI: 10.1016/j.chembiol.2005.09.015 Copyright © 2005 Elsevier Ltd Terms and Conditions

Figure 1 Structures of Metabolites Isolated from Alternaria solani Chemistry & Biology 2005 12, 1301-1309DOI: (10.1016/j.chembiol.2005.09.015) Copyright © 2005 Elsevier Ltd Terms and Conditions

Figure 2 RD-PKS Architecture and SDS-PAGE Analysis of A. oryzae Transformants (A) Architecture of the PKSN polyketide synthase from Alternaria solani and other fungal reduced complex-type polyketide synthases. Schematic organization of domains β-ketoacyl synthase (KS), acyltransferase (AT), dehydratase (DH), C-methyltransferase (CMeT), enoyl reductase (ER), β-ketoreductase (KR), and acyl carrier protein (ACP) of PKSN, FUM1p (AAD43562, Gibberella moniliformis), LDKS (AAD34559, Aspergillus terrues), LNKS (AAD39830, Aspergillus terreus), MlcA (BAC20564, Penicillium citrinum), MlcB (BAC20566, Penicillium citrinum), and PKS1 (AAB08104, Cochliobolus heterostrophus). PSED is a homolog of a peptide synthase elongation domain. (B) Heterologous expression of PKSN. SDS-PAGE analysis: lane 1, 100 k g precipitate of A. oryzae/pTAex3R extract; lane 2, 100 k g precipitate of A. oryzae/pTA-PKSN10a extract; lane 3, 210 k g supernatant of A. oryzae/pTAex3R extract; lane 4, 210 k g supernatant of A. oryzae/pTA-PKSN10a extract; lane 5, 210 k g precipitate of A. oryzae/pTAex3R extract; lane 6, 210 k g precipitate of A. oryzae/pTA-PKSN10a extract; and lane 7, molecular weight markers. Chemistry & Biology 2005 12, 1301-1309DOI: (10.1016/j.chembiol.2005.09.015) Copyright © 2005 Elsevier Ltd Terms and Conditions

Figure 3 LC-MS Analysis of Product from the Transformant Aspergillus oryzae/pTA-PKSN10a (A) Total positive ion chromatogram. (B) Total negative ion chromatogram. (C) Mass spectrum of the peak Rt = 13.3 min in (A). (D) Mass spectrum of the peak Rt = 13.3 min in (B). Chemistry & Biology 2005 12, 1301-1309DOI: (10.1016/j.chembiol.2005.09.015) Copyright © 2005 Elsevier Ltd Terms and Conditions

Figure 4 Proposed Biosynthesis of Alternapyrone Catalyzed by PKSN Chemistry & Biology 2005 12, 1301-1309DOI: (10.1016/j.chembiol.2005.09.015) Copyright © 2005 Elsevier Ltd Terms and Conditions

Figure 5 Amino Acid Sequence Alignment of C-Methyltransferase Domains in Fungal Iterative Type I Polyketide Synthases An asterisk (∗) marks completely conserved amino acid residues, whereas a colon (:) identifies highly conserved residues and a period (.) indicates moderately conserved residues. Numbers I, II, III, and IV correspond to consensus motifs I–IV following the definition of Anderson and coworkers [30]. Their putative key amino acids are shown in black. Chemistry & Biology 2005 12, 1301-1309DOI: (10.1016/j.chembiol.2005.09.015) Copyright © 2005 Elsevier Ltd Terms and Conditions