The Enzyme Database

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EC 1.1.1.437     
Accepted name: 5-dehydrofumagillol 5-reductase
Reaction: fumagillol + NADP+ = 5-dehydrofumagillol + NADPH + H+
For diagram of reaction, click here
Glossary: fumagillol = (3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-ol
Other name(s): af490 (gene name); Fma-KR
Systematic name: fumagillol:NADP+ 5-oxidoreductase
Comments: The enzyme, characterized from the mold Aspergillus fumigatus, participates in the biosynthesis of the meroterpenoid fumagillin. It is a partial polyketide synthase (PKS) consisting of only a dehydratase (DH) and a ketoreductase (KR) domain.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Lin, H.C., Tsunematsu, Y., Dhingra, S., Xu, W., Fukutomi, M., Chooi, Y.H., Cane, D.E., Calvo, A.M., Watanabe, K. and Tang, Y. Generation of complexity in fungal terpene biosynthesis: discovery of a multifunctional cytochrome P450 in the fumagillin pathway. J. Am. Chem. Soc. 136 (2014) 4426–4436. [DOI] [PMID: 24568283]
[EC 1.1.1.437 created 2022]
 
 
EC 1.14.11.82     
Accepted name: 5-dehydro-6-demethoxyfumagillol dioxygenase
Reaction: 5-dehydro-6-demethoxyfumagillol + 2-oxoglutarate + O2 = 5-dehydro-6-demethoxy-6-hydroxyfumagillol + succinate + CO2
For diagram of santalene and bergamotene biosynthesis, click here
Glossary: fumagillol = (3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-ol
Other name(s): fmaF (gene name); Fma-C6H
Systematic name: 5-dehydro-6-demethoxyfumagillol,2-oxoglutarate:oxygen oxidoreductase (6-hydroxylating)
Comments: Requires iron(II). The enzyme, characterized from the mold Aspergillus fumigatus, participates in the biosynthesis of the meroterpenoid fumagillin.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Lin, H.C., Tsunematsu, Y., Dhingra, S., Xu, W., Fukutomi, M., Chooi, Y.H., Cane, D.E., Calvo, A.M., Watanabe, K. and Tang, Y. Generation of complexity in fungal terpene biosynthesis: discovery of a multifunctional cytochrome P450 in the fumagillin pathway. J. Am. Chem. Soc. 136 (2014) 4426–4436. [DOI] [PMID: 24568283]
[EC 1.14.11.82 created 2022]
 
 
EC 1.14.14.184     
Accepted name: 5-dehydro-6-demethoxyfumagillol synthase
Reaction: (+)-exo-β-bergamotene + 2 [reduced NADPH—hemoprotein reductase] + 3 O2 = 5-dehydro-6-demethoxyfumagillol + 2 [oxidized NADPH—hemoprotein reductase] + 3 H2O (overall reaction)
(1a) (+)-exo-β-bergamotene + [reduced NADPH—hemoprotein reductase] + O2 = (5R)-hydroxy-(+)-exo-β-bergamotene + [oxidized NADPH—hemoprotein reductase] + H2O
(1b) (5R)-hydroxy-(+)-exo-β-bergamotene + O2 = (3S)-3-[2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-4-methylidenecyclohexan-1-one + H2O
(1c) (3S)-3-[2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-4-methylidenecyclohexan-1-one + [reduced NADPH—hemoprotein reductase] + O2 = 5-dehydro-6-demethoxyfumagillol + [oxidized NADPH—hemoprotein reductase] + H2O
For diagram of reaction, click here and for diagram of santalene and bergamotene biosynthesis, click here
Glossary: (+)-exo-β-bergamotene = β-trans-bergamotene = (1S,5S,6R)-6-methyl-2-methylidene-6-(4-methylpent-3-enyl)bicyclo[3.1.1]heptane
fumagillol = (3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-ol
fumagillin = (2E,4E,6E,8E)-10-({(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]oct-6-yl}oxy)-10-oxodeca-2,4,6,8-tetraenoate
Other name(s): fumagillin multifunctional cytochrome P450 monooxygenase; Fma-P450; fmaG (gene name)
Systematic name: (+)-exo-β-bergamotene,[reduced NADPH—hemoprotein reductase] oxidoreductase (5-dehydro-6-demethoxyfumagillol-producing)
Comments: The enzyme, characterized from the mold Aspergillus fumigatus, catalyses a complex transformation comprising hydroxylation, bicyclic ring-opening, and two epoxidations, generating the sesquiterpenoid core skeleton of fumagillin.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Lin, H.C., Tsunematsu, Y., Dhingra, S., Xu, W., Fukutomi, M., Chooi, Y.H., Cane, D.E., Calvo, A.M., Watanabe, K. and Tang, Y. Generation of complexity in fungal terpene biosynthesis: discovery of a multifunctional cytochrome P450 in the fumagillin pathway. J. Am. Chem. Soc. 136 (2014) 4426–4436. [DOI] [PMID: 24568283]
[EC 1.14.14.184 created 2022]
 
 
EC 2.1.1.387     
Accepted name: 5-dehydro-6-demethoxy-6-hydroxyfumagillol O-methyltransferase
Reaction: S-adenosyl-L-methionine + 5-dehydro-6-demethoxy-6-hydroxyfumagillol = S-adenosyl-L-homocysteine + 5-dehydrofumagillol
For diagram of reaction, click here
Glossary: fumagillol = (3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-ol
Other name(s): Fma-MT; fmaD (gene name); af390-400 (gene name)
Systematic name: S-adenosyl-L-methionine:5-dehydro-6-demethoxy-6-hydroxyfumagillol 6-O-methyltransferase
Comments: The enzyme, characterized from the mold Aspergillus fumigatus, participates in the biosynthesis of the meroterpenoid fumagillin.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Lin, H.C., Tsunematsu, Y., Dhingra, S., Xu, W., Fukutomi, M., Chooi, Y.H., Cane, D.E., Calvo, A.M., Watanabe, K. and Tang, Y. Generation of complexity in fungal terpene biosynthesis: discovery of a multifunctional cytochrome P450 in the fumagillin pathway. J. Am. Chem. Soc. 136 (2014) 4426–4436. [DOI] [PMID: 24568283]
[EC 2.1.1.387 created 2022]
 
 


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