The Enzyme Database

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EC 1.1.3.42     
Accepted name: prosolanapyrone-II oxidase
Reaction: prosolanapyrone II + O2 = prosolanapyrone III + H2O2
For diagram of solanapyrone biosynthesis, click here
Glossary: prosolanapyrone II = 3-(hydroxymethyl)-4-methoxy-6-(1E,7E,9E)-undeca-1,7,9-trien-1-yl-2H-pyran-2-one
prosolanapyrone III = 4-methoxy-2-oxo-6-(1E,7E,9E)-undeca-1,7,9-trien-1-yl-2H-pyran-3-carboxaldehyde
Other name(s): Sol5 (ambiguous); SPS (ambiguous); solanapyrone synthase (bifunctional enzyme: prosolanapyrone II oxidase/prosolanapyrone III cycloisomerase); prosolanapyrone II oxidase
Systematic name: prosolanapyrone-II:oxygen 3′-oxidoreductase
Comments: The enzyme is involved in the biosynthesis of the phytotoxin solanapyrone by some fungi. The bifunctional enzyme catalyses the oxidation of prosolanapyrone II and the subsequent Diels Alder cycloisomerization of the product prosolanapyrone III to (-)-solanapyrone A (cf. EC 5.5.1.20, prosolanapyrone III cycloisomerase).
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Kasahara, K., Miyamoto, T., Fujimoto, T., Oguri, H., Tokiwano, T., Oikawa, H., Ebizuka, Y. and Fujii, I. Solanapyrone synthase, a possible Diels-Alderase and iterative type I polyketide synthase encoded in a biosynthetic gene cluster from Alternaria solani. ChemBioChem 11 (2010) 1245–1252. [DOI] [PMID: 20486243]
2.  Katayama, K., Kobayashi, T., Oikawa, H., Honma, M. and Ichihara, A. Enzymatic activity and partial purification of solanapyrone synthase: first enzyme catalyzing Diels-Alder reaction. Biochim. Biophys. Acta 1384 (1998) 387–395. [DOI] [PMID: 9659400]
3.  Katayama, K., Kobayashi, T., Chijimatsu, M., Ichihara, A. and Oikawa, H. Purification and N-terminal amino acid sequence of solanapyrone synthase, a natural Diels-Alderase from Alternaria solani. Biosci. Biotechnol. Biochem. 72 (2008) 604–607. [DOI] [PMID: 18256508]
[EC 1.1.3.42 created 2011]
 
 
EC 5.5.1.20     
Accepted name: prosolanapyrone-III cycloisomerase
Reaction: prosolanapyrone III = (–)-solanapyrone A
For diagram of solanapyrone biosynthesis, click here
Glossary: prosolanapyrone III = 4-methoxy-2-oxo-6-(1E,7E,9E)-undeca-1,7,9-trien-1-yl-2H-pyran-3-carboxaldehyde
(–)-solanapyrone A = 4-methoxy-6-((1R,2S,4aR,8aR)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)-2-oxo-2H-pyran-3-carboxaldehyde
Other name(s): Sol5 (ambiguous); SPS (ambiguous); solanapyrone synthase (bifunctional enzyme: prosolanapyrone II oxidase/prosolanapyrone III cyclosiomerase)
Systematic name: prosolanapyrone-III:(–)-solanapyrone A isomerase
Comments: The enzyme is involved in the biosynthesis of the phytotoxin solanapyrone in some fungi. The bifunctional enzyme catalyses the oxidation of prosolanapyrone II and the subsequent Diels Alder cycloisomerization of the product prosolanapyrone III to (–)-solanapyrone A (cf. EC 1.1.3.42, prosolanapyrone II oxidase).
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Kasahara, K., Miyamoto, T., Fujimoto, T., Oguri, H., Tokiwano, T., Oikawa, H., Ebizuka, Y. and Fujii, I. Solanapyrone synthase, a possible Diels-Alderase and iterative type I polyketide synthase encoded in a biosynthetic gene cluster from Alternaria solani. ChemBioChem 11 (2010) 1245–1252. [DOI] [PMID: 20486243]
2.  Katayama, K., Kobayashi, T., Oikawa, H., Honma, M. and Ichihara, A. Enzymatic activity and partial purification of solanapyrone synthase: first enzyme catalyzing Diels-Alder reaction. Biochim. Biophys. Acta 1384 (1998) 387–395. [DOI] [PMID: 9659400]
3.  Katayama, K., Kobayashi, T., Chijimatsu, M., Ichihara, A. and Oikawa, H. Purification and N-terminal amino acid sequence of solanapyrone synthase, a natural Diels-Alderase from Alternaria solani. Biosci. Biotechnol. Biochem. 72 (2008) 604–607. [DOI] [PMID: 18256508]
[EC 5.5.1.20 created 2011]
 
 


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