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IUBMB Comments Isolated from the fungus Aspergillus clavatus . The product is a sesterterpenoid (C25
Synonyms
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ACLA_76850
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(2E,6E,10E,14E)-geranylfarnesyl diphosphate + H2O = ophiobolin F + diphosphate
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MetaCyc
ophiobolin F biosynthesis
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(2E,6E,10E,14E)-geranylfarnesyl-diphosphate diphosphate-lyase (cyclizing, ophiobolin-F-forming)
Isolated from the fungus Aspergillus clavatus. The product is a sesterterpenoid (C25 terpenoid).
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(2E,6E,10E,14E)-geranylfarnesyl diphosphate + H2O
ophiobolin F + diphosphate
(2E,6E,10E,14E)-geranylfarnesyl diphosphate + H2O
ophiobolin F + diphosphate
Substrates: -
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(2E,6E,10E,14E)-geranylfarnesyl diphosphate + H2O
ophiobolin F + diphosphate
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Substrates: -
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(2E,6E,10E,14E)-geranylfarnesyl diphosphate + H2O
ophiobolin F + diphosphate
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Substrates: -
?
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(2E,6E,10E,14E)-geranylfarnesyl diphosphate + H2O
ophiobolin F + diphosphate
(2E,6E,10E,14E)-geranylfarnesyl diphosphate + H2O
ophiobolin F + diphosphate
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Substrates: -
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(2E,6E,10E,14E)-geranylfarnesyl diphosphate + H2O
ophiobolin F + diphosphate
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Substrates: -
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Mg2+
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used in assay conditions
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cf. EC 2.5.1.29
UniProt
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UniProt
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Highest Expressing Human Cell Lines
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Cell Line Links
Gene Links
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physiological function
Aspergillus oryzae expressing ophiolon synthase F accumulates ophiolbolin F in ints mycelium
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OBLA_EMEVA
728
0
82233
Swiss-Prot
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OBLA_ASPCI
725
0
82262
Swiss-Prot
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OBLA_ASPCL
Aspergillus clavatus (strain ATCC 1007 / CBS 513.65 / DSM 816 / NCTC 3887 / NRRL 1 / QM 1276 / 107)
718
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81603
Swiss-Prot
other Location (Reliability: 5 )
OBLA_COCH5
Cochliobolus heterostrophus (strain C5 / ATCC 48332 / race O)
721
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81421
Swiss-Prot
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A0A6G7GHF5_ASPUT
725
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82262
TrEMBL
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D87E
almost 2fold increase in ophiobolin F production
E95V
more than 1.5fold increase in ophiobolin F production
H190F
almost 2fold increase in ophiobolin F production
Q122D
almost 1.5fold increase in ophiobolin F production
R131K
more than 1.5fold increase in ophiobolin F production
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Ni-NTA column chromatography
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expressed in Escherichia coli
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synthesis
synthesis of ophiolbolin F in Escherichia coli. Overexpression of codon-optimized gene Au8003 results in a detectable production of ophiobolin F. Addition of arabinose allows a more than 10fold improvement of production than that of glycerol. Assembly of the whole mevalonate pathway and an additional copy of isopentenyl diphosphate isomerase gene lead to approximately 24fold and 60fold yield increases, respectively. Further optimization and the expression of short-chain terpene synthase C15 synthase lead to a yield of 82.76 mg/l at 96 h. Further protein engineering including mutations on the rate-limiting cyclization part of Au8003 enable a further yield improvement (> 150 mg/l at 96 h) in shake flasks
synthesis
expression of the ophiolin F synthase gene in Aspergillus oryzae allows to obtain 17 mg/l of pure compound by fermentation
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Chiba, R.; Minami, A.; Gomi, K.; Oikawa, H.
Identification of ophiobolin F synthase by a genome mining approach: a sesterterpene synthase from Aspergillus clavatus
Org. Lett.
15
594-597
2013
Aspergillus clavatus, Aspergillus clavatus NRRL 1
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Yuan, W.; Lv, S.; Chen, L.; Zhao, Y.; Deng, Z.; Hong, K.
Production of sesterterpene ophiobolin by a bifunctional terpene synthase in Escherichia coli
Appl. Microbiol. Biotechnol.
103
8785-8797
2019
Aspergillus ustus (A0A6G7GHF5)
brenda
Quan, Z.; Dickschat, J.S.
On the mechanism of ophiobolin F synthase and the absolute configuration of its product by isotopic labelling experiments
Org. Biomol. Chem.
18
6072-6076
2020
Aspergillus calidoustus (A0A0U5G0B1)
brenda
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