4.2.3.6: trichodiene synthase
This is an abbreviated version!
For detailed information about trichodiene synthase, go to the full flat file.
Word Map on EC 4.2.3.6
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4.2.3.6
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trichothecene
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mycotoxin
-
graminearum
-
sesquiterpene
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sporotrichioides
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deoxynivalenol
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trichothecene-producing
-
culmorum
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gibberella
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trichodermin
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carbocation
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stachybotrys
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chartarum
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pulicaris
-
5-epi-aristolochene
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bisabolyl
-
biotechnology
- 4.2.3.6
-
trichothecene
-
mycotoxin
- graminearum
-
sesquiterpene
- sporotrichioides
-
deoxynivalenol
-
trichothecene-producing
- culmorum
- gibberella
-
trichodermin
-
carbocation
- stachybotrys
- chartarum
- pulicaris
- 5-epi-aristolochene
-
bisabolyl
- biotechnology
Reaction
Synonyms
EC 4.1.99.6, sesquiterpene cyclase, synthase, trichodiene, TDN synthase, trans,trans-farnesyl-diphosphate sesquiterpenoid-lyase, tri5, trichodiene synthase, trichodiene synthetase
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Reference on EC 4.2.3.6 - trichodiene synthase
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REF. 
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Hohn, T.M.; Vanmiddlesworth, F.
Purification and characterization of the sesquiterpene cyclase trichodiene synthetase from Fusarium sporotrichioides
Arch. Biochem. Biophys.
251
756-761
1986
Fusarium sporotrichioides
Cane, D.E.; Yang, G.; Xue, Q.; Shim, J.H.
Trichodiene synthase. Substrate specificity and inhibition
Biochemistry
34
2471-2479
1995
Fusarium sporotrichioides
Cane, D.E.; Shim, J.H.; Xue, Q.; Fitzsimons, B.C.
Trichodiene synthase. Identification of active site residues by site-directed mutagenesis
Biochemistry
34
2480-2488
1995
Fusarium sambucinum, Fusarium sporotrichioides
Cane, D.E.; Ha, H.J.
Trichodiene biosynthesis and the enzymatic cyclization of nerolidyl pyrophosphate
J. Am. Chem. Soc.
108
3097-3099
1986
Fusarium sporotrichioides, Trichothecium roseum
-
Cane, D.E.; Yang, G.
Trichodiene syntase. Stereochemical studies of the cryptic allylic diphosphate isomerase activity using an anomalous substrate
J. Org. Chem.
59
5794-5798
1994
Escherichia coli, Fusarium sporotrichioides
-
Cane, D.E.; Pawlak, J.L.; Horak, R.M.
Studies of the cryptic allylic pyrophosphate isomerase activity of trichodiene synthase using the anomalous substrate 6,7-dihydrofarnesyl pyrophosphate
Biochemistry
29
5476-5490
1990
Fusarium sporotrichioides
Evans, R.; Hanson, J.R.
Studies in terpenoid biosynthesis. Part XIV. Formation of the sesquiterpene trichodiene
J. Chem. Soc. Perkin Trans. I
1976
326-329
1976
Trichothecium roseum
Hohn, T.M.; Beremand, M.N.
Regulation of trichodiene synthase in Fusarium sporotrichioides and Gibberella pulicaris (Fusarium sambucinum)
Appl. Environ. Microbiol.
55
1500-1503
1989
Fusarium sambucinum, Fusarium sporotrichioides, Fusarium sporotrichioides NRLL 3299
Hohn, T.M.; Beremand, P.D.
Isolation and nucleotide sequence of a sesquiterpene cyclase gene from the trichothecene-producing fungus Fusarium sporotrichioides
Gene
79
131-138
1989
Fusarium sporotrichioides
Hohn, T.M.; Plattner, R.D.
Expression of the trichodiene synthase gene of Fusarium sporotrichioides in Escherichia coli results in sesquiterpene production
Arch. Biochem. Biophys.
275
92-97
1989
Fusarium sporotrichioides
Hohn, T.M.; Ohlrogge, J.B.
Expression of a fungal sesquiterpene cyclase in transgenic tobacco
Plant Physiol.
97
460-462
1991
Fusarium sporotrichioides
Cane, D.E.; Xue, Q.
Trichodiene Synthase. Enzymic Formation of Multiple Sesquiterpenes by Alteration of the Cyclase Active Site
J. Am. Chem. Soc.
118
1563-1564
1996
Fusarium sporotrichioides
-
Cane, D.E.; Chiu, H.T.; Liang, P.H.; Anderson, K.S.
Pre-steady-state kinetic analysis of the trichodiene synthase reaction pathway
Biochemistry
36
8332-8339
1997
Fusarium sporotrichioides
Cane, D.E.; Xue, Q.; Fitzsimons, B.C.
Trichodiene synthase. Probing the role of the highly conserved aspartate-rich region by site-directed mutagenesis
Biochemistry
35
12369-12376
1996
Fusarium sporotrichioides
Cane, D.E.; Bowser, T.E.
Trichodiene synthase: mechanism-based inhibition of a sesquiterpene cyclase
Bioorg. Med. Chem. Lett.
9
1127-1132
1999
Fusarium sporotrichioides
Rynkiewicz, M.J.; Cane, D.E.; Christianson, D.W.
X-ray crystal structures of D100E trichodiene synthase and its pyrophosphate complex reveal the basis for terpene product diversity
Biochemistry
41
1732-1741
2002
Fusarium sporotrichioides (P13513)
Rynkiewicz, M.J.; Cane, D.E.; Christianson, D.W.
Structure of trichodiene synthase from Fusarium sporotrichioides provides mechanistic inferences on the terpene cyclization cascade
Proc. Natl. Acad. Sci. USA
98
13543-13548
2001
Fusarium sporotrichioides (P13513), Fusarium sporotrichioides
Vedula, L.S.; Cane, D.E.; Christianson, D.W.
Role of arginine-304 in the diphosphate-triggered active site closure mechanism of trichodiene synthase
Biochemistry
44
12719-12727
2005
Fusarium sporotrichioides (P13513)
Vedula, L.S.; Rynkiewicz, M.J.; Pyun, H.J.; Coates, R.M.; Cane, D.E.; Christianson, D.W.
Molecular recognition of the substrate diphosphate group governs product diversity in trichodiene synthase mutants
Biochemistry
44
6153-6163
2005
Fusarium sporotrichioides (P13513)
Vedula, L.S.; Zhao, Y.; Coates, R.M.; Koyama, T.; Cane, D.E.; Christianson, D.W.
Exploring biosynthetic diversity with trichodiene synthase
Arch. Biochem. Biophys.
466
260-266
2007
Fusarium sporotrichioides
Vedula, L.S.; Jiang, J.; Zakharian, T.; Cane, D.E.; Christianson, D.W.
Structural and mechanistic analysis of trichodiene synthase using site-directed mutagenesis: probing the catalytic function of tyrosine-295 and the asparagine-225/serine-229/glutamate-233-Mg2+B motif
Arch. Biochem. Biophys.
469
184-194
2008
Fusarium sporotrichioides (P13513), Fusarium sporotrichioides
Cuzick, A.; Urban, M.; Hammond-Kosack, K.
Fusarium graminearum gene deletion mutants map1 and tri5 reveal similarities and differences in the pathogenicity requirements to cause disease on Arabidopsis and wheat floral tissue
New Phytol.
177
990-1000
2008
Fusarium graminearum (Q00909), Fusarium graminearum, Fusarium graminearum PH-1 (Q00909)
Ilgen, P.; Hadeler, B.; Maier, F.J.; Schaefer, W.
Developing kernel and rachis node induce the trichothecene pathway of Fusarium graminearum during wheat head infection
Mol. Plant Microbe Interact.
22
899-908
2009
Fusarium graminearum
Koster, B.; Wong, B.; Straus, N.; Malloch, D.
A multi-gene phylogeny for Stachybotrys evidences lack of trichodiene synthase (tri5) gene for isolates of one of three intrageneric lineages
Mycol. Res.
113
877-886
2009
Stachybotrys microspora (D0FL83), Stachybotrys microspora (D0FL90), Stachybotrys cylindrospora (D0FL84), Stachybotrys cylindrospora (D0FL88), Memnoniella echinata (D0FL85), Stachybotrys kampalensis (D0FL86), Stachybotrys kampalensis (D0FL89), Memnoniella dichroa (D0FL91), Fusarium sporotrichioides (D0FL92), Trichothecium roseum (D0FL93), Paramyrothecium roridum (D0FL95), Memnoniella echinata CBS 304.54 (D0FL85), Stachybotrys microspora CBS 186.79 (D0FL83), Stachybotrys microspora UAMH 7747 (D0FL90), Trichothecium roseum DAOM 57205 (D0FL93), Trichothecium roseum UAMH 7839 (D0FL93), Fusarium sporotrichioides UAMH 5334 (D0FL92), Stachybotrys kampalensis UAMH 7746 (D0FL89), Stachybotrys cylindrospora UAMH 7122 (D0FL88), Memnoniella echinata UAMH 3195 (D0FL85), Stachybotrys kampalensis CBS 388.73 (D0FL86), Stachybotrys cylindrospora CBS 203.61 (D0FL84), Paramyrothecium roridum UAMH 1369 (D0FL95), Memnoniella dichroa UAMH 7748 (D0FL91)
Hong, Y.J.; Tantillo, D.J.
Modes of inactivation of trichodiene synthase by a cyclopropane-containing farnesyldiphosphate analog
Org. Biomol. Chem.
7
4101-4109
2009
Fusarium sporotrichioides
Tijerino, A.; Cardoza, R.E.; Moraga, J.; Malmierca, M.G.; Vicente, F.; Aleu, J.; Collado, I.G.; Gutierrez, S.; Monte, E.; Hermosa, R.
Overexpression of the trichodiene synthase gene tri5 increases trichodermin production and antimicrobial activity in Trichoderma brevicompactum
Fungal Genet. Biol.
48
285-296
2011
Trichoderma brevicompactum (F4MJM0), Trichoderma brevicompactum, Trichoderma brevicompactum IBT40841 (F4MJM0)
Dickschat, J.S.; Brock, N.L.; Citron, C.A.; Tudzynski, B.
Biosynthesis of sesquiterpenes by the fungus Fusarium verticillioides
ChemBioChem
12
2088-2095
2011
Fusarium verticillioides, Fusarium verticillioides NRRL 20956
Malmierca, M.; Mccormick, S.; Cardoza, R.; Alexander, N.; Monte, E.; Gutierrez, S.
Production of trichodiene by Trichoderma harzianum alters the perception of this biocontrol strain by plants and antagonized fungi
Environ. Microbiol.
17
2628-2646
2015
Trichoderma harzianum (Q6A1B7)
Burkhardt, I.; Dickschat, J.S.
The absolute configuration of isochamigrene new insights into the cyclisation mechanism of trichodiene synthase
Chem. Commun. (Camb.)
54
3540-3542
2018
Fusarium sporotrichioides, Fusarium sporotrichioides DSM 62425
Kumari, I.; Chaudhary, N.; Sandhu, P.; Ahmed, M.; Akhter, Y.
Structural and mechanistic analysis of engineered trichodiene synthase enzymes from Trichoderma harzianum towards higher catalytic activities empowering sustainable agriculture
J. Biomol. Struct. Dyn.
34
1176-1189
2016
Trichoderma harzianum
Maeda, K.; Nakajima, Y.; Motoyama, T.; Kondoh, Y.; Kawamura, T.; Kanamaru, K.; Ohsato, S.; Nishiuchi, T.; Yoshida, M.; Osada, H.; Kobayashi, T.; Kimura, M.
Identification of a trichothecene production inhibitor by chemical array and library screening using trichodiene synthase as a target protein
Pestic. Biochem. Physiol.
138
1-7
2017
Fusarium graminearum, Fusarium graminearum JCM9873
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