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Solanapyrone Synthase, a Possible Diels–Alderase and Iterative Type I Polyketide Synthase Encoded in a Biosynthetic Gene Cluster from Alternaria solani

  1. Ken Kasahara  Dr.2,4,
  2. Takanori Miyamoto2,
  3. Takashi Fujimoto3,
  4. Hiroki Oguri Dr.3,
  5. Tetsuo Tokiwano  Dr.3,5,
  6. Hideaki Oikawa Prof.3,
  7. Yutaka Ebizuka Prof.2,
  8. Isao Fujii Prof.1

Article first published online: 19 MAY 2010

DOI: 10.1002/cbic.201000173

Issue

ChemBioChem

ChemBioChem

Volume 11, Issue 9, pages 1245–1252, June 14, 2010

Additional Information

How to Cite

Kasahara , K., Miyamoto, T., Fujimoto, T., Oguri, H., Tokiwano , T., Oikawa, H., Ebizuka, Y. and Fujii, I. (2010), Solanapyrone Synthase, a Possible Diels–Alderase and Iterative Type I Polyketide Synthase Encoded in a Biosynthetic Gene Cluster from Alternaria solani. ChemBioChem, 11: 1245–1252. doi: 10.1002/cbic.201000173

Author Information

  1. 1

    School of Pharmacy, Iwate Medical University, 2-1-1 Nishitokuta, Yahaba, Iwate 028-3694 (Japan), Fax: (+81) 19-698-1923

  2. 2

    Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)

  3. 3

    Graduate School of Science, Hokkaido University, Kita 10 Nishi 8, Sapporo 060-0810 (Japan)

  4. 4

    Present address: Neo-Morgan Laboratory Inc., Biotechnology Research Center, Teikyo University, 907 Nogawa, Miyamae-ku, Kawasaki, Kanagawa 216-0001 (Japan)

  5. 5

    Present address: Faculty of Bioresource Sciences, Akita Prefectural University, Akita 010-0195 (Japan)

Publication History

  1. Issue published online: 7 JUN 2010
  2. Article first published online: 19 MAY 2010
  3. Manuscript Received: 16 MAR 2010

Funded by

  • Japan Society for the Promotion of Science
  • Ministry of Education, Culture, Sports, Science and Technology of Japan. Grant Number: 19310139

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Keywords:

  • biological Diels–Alder reaction;
  • biosynthesis;
  • gene sequencing;
  • polyketide synthases;
  • solanapyrone

Abstract

The solanapyrone biosynthetic gene cluster was cloned from Alternaria solani. It consists of six genes—sol1–6—coding for a polyketide synthase, an O-methyltransferase, a dehydrogenase, a transcription factor, a flavin-dependent oxidase, and cytochrome P450. The prosolanapyrone synthase (PSS) encoded by sol1 was expressed in Aspergillus oryzae and its product was identified as desmethylprosolanapyrone I (8). Although PSS is closely related to the PKSs/Diels–Alderases LovB and MlcA of lovastatin and compactin biosynthesis, it did not catalyze cycloaddition. Sol5, encoding a flavin-dependent oxidase (solanapyrone synthase, SPS), was expressed in Pichia pastoris and purified. The purified recombinant SPS showed activity for the formation of (−)-solanapyrone A (1) from achiral prosolanapyrone II (2), establishing that this single enzyme catalyzes both the oxidation and the subsequent cycloaddition reaction, possibly as a Diels–Alder enzyme.

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