Reference on EC 4.2.3.9 - aristolochene synthase
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REF. 
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Cane, D.E.; Prabhakaran, P.C.; Oliver, J.S.; McIlwaine, D.B.
Aristolochene biosynthesis. Stereochemistry of the deprotonation steps in the enzymatic cyclization of farnesyl pyrophosphate
J. Am. Chem. Soc.
112
3209-3210
1990
Aspergillus terreus
-
Cane, D.E.; Prabhakaran, P.C.; Salaski, E.J.; Harrison, P.M.H.; Noguchi, H.; Rawlings, B.J.
Aristolochene biosynthesis and enzymatic cyclization of farnesyl pyrophosphate
J. Am. Chem. Soc.
111
8914-8916
1989
Aspergillus terreus
-
Hohn, T.M.; Plattner, R.D.
Purification and characterization of the sesquiterpene cyclase aristolochene synthase from Penicillium roqueforti
Arch. Biochem. Biophys.
272
137-143
1989
Penicillium roqueforti
Proctor, R.H.; Hohn, T.M.
Aristolochene synthase. Isolation, characterization, and bacterial expression of a sesquiterpenoid biosynthetic gene (Ari1) from Penicillium roqueforti
J. Biol. Chem.
268
4543-4548
1993
Penicillium roqueforti
Caruthers, J.M.; Kang, I.; Rynkiewicz, M.J.; Cane, D.E.; Christianson, D.W.
Crystal structure determination of aristolochene synthase from the blue cheese mold, Penicillium roqueforti
J. Biol. Chem.
275
25533-25539
2000
Penicillium roqueforti
Calvert, M.J.; Taylor, S.E.; Allemann, R.K.
Tyrosine 92 of aristolochene synthase directs cyclisation of farnesyl pyrophosphate
Chem. Commun. (Camb.)
2002
2384-2385
2002
Penicillium roqueforti
-
Calvert, M.J.; Ashton, P.R.; Allemann, R.K.
Germacrene A is a product of the aristolochene synthase-mediated conversion of farnesylpyrophosphate to aristolochene
J. Am. Chem. Soc.
124
11636-11641
2002
Penicillium roqueforti
Deligeorgopoulou, A.; Allemann, R.K.
Evidence for differential folding of farnesyl pyrophosphate in the active site of aristolochene synthase: a single-point mutation converts aristolochene synthase into an (E)-b-farnesene synthase
Biochemistry
42
7741-7747
2003
Penicillium roqueforti, Penicillium roqueforti (Q03471)
Cane, D.E.; Kang, I.
Aristolochene synthase: purification, molecular cloning, high-level expression in Escherichia coli, and characterization of the Aspergillus terreus cyclase
Arch. Biochem. Biophys.
376
354-364
2000
Aspergillus terreus, Penicillium roqueforti
Forcat, S.; Allemann, R.K.
Dual role for phenylalanine 178 during catalysis by aristolochene synthase
Chem. Commun. (Camb.)
2004
2094-2095
2004
Penicillium roqueforti
Felicetti, B.; Cane, D.E.
Aristolochene synthase: mechanistic analysis of active site residues by site-directed mutagenesis
J. Am. Chem. Soc.
126
7212-7221
2004
Aspergillus terreus, Penicillium roqueforti (Q03471), Penicillium roqueforti
Shishova, E.Y.; Di Costanzo, L.; Cane, D.E.; Christianson, D.W.
X-ray crystal structure of aristolochene synthase from Aspergillus terreus and evolution of templates for the cyclization of farnesyl diphosphate
Biochemistry
46
1941-1951
2007
Aspergillus terreus (Q9UR08), Aspergillus terreus
Yu, F.; Miller, D.J.; Allemann, R.K.
Probing the reaction mechanism of aristolochene synthase with 12,13-difluorofarnesyl diphosphate
Chem. Commun. (Camb. )
2007
4155-4157
2007
Escherichia coli
Miller, D.J.; Yu, F.; Allemann, R.K.
Aristolochene synthase-catalyzed cyclization of 2-fluorofarnesyl-diphosphate to 2-fluorogermacrene A
ChemBioChem
8
1819-1825
2007
Penicillium roqueforti
Allemann, R.K.; Young, N.J.; Ma, S.; Truhlar, D.G.; Gao, J.
Synthetic efficiency in enzyme mechanisms involving carbocations: aristolochene synthase
J. Am. Chem. Soc.
129
13008-13013
2007
Penicillium roqueforti (Q03471)
Forcat, S.; Allemann, R.K.
Stabilisation of transition states prior to and following eudesmane cation in aristolochene synthase
Org. Biomol. Chem.
4
2563-2567
2006
Penicillium roqueforti
Miller, D.J.; Yu, F.; Young, N.J.; Allemann, R.K.
Competitive inhibition of aristolochene synthase by phenyl-substituted farnesyl diphosphates: evidence of active site plasticity
Org. Biomol. Chem.
5
3287-3298
2007
Penicillium roqueforti (Q03471), Penicillium roqueforti
Christianson, D.W.
Unearthing the roots of the terpenome
Curr. Opin. Chem. Biol.
12
141-150
2008
Aspergillus terreus
Shishova, E.Y.; Yu, F.; Miller, D.J.; Faraldos, J.A.; Zhao, Y.; Coates, R.M.; Allemann, R.K.; Cane, D.E.; Christianson, D.W.
X-ray crystallographic studies of substrate binding to aristolochene synthase suggest a metal ion binding sequence for catalysis
J. Biol. Chem.
283
15431-15439
2008
Aspergillus terreus (Q9UR08), Aspergillus terreus
Miller, D.J.; Gao, J.; Truhlar, D.G.; Young, N.J.; Gonzalez, V.; Allemann, R.K.
Stereochemistry of eudesmane cation formation during catalysis by aristolochene synthase from Penicillium roqueforti
Org. Biomol. Chem.
6
2346-2354
2008
Penicillium roqueforti
Faraldos, J.A.; OMaille, P.E.; Dellas, N.; Noel, J.P.; Coates, R.M.
Bisabolyl-derived sesquiterpenes from tobacco 5-epi-aristolochene synthase-catalyzed cyclization of (2Z,6E)-farnesyl diphosphate
J. Am. Chem. Soc.
132
4281-4289
2010
Nicotiana tabacum
Faraldos, J.A.; Kariuki, B.; Allemann, R.K.
Intermediacy of eudesmane cation during catalysis by aristolochene synthase
J. Org. Chem.
75
1119-1125
2010
Penicillium roqueforti
Miller, D.J.; Yu, F.; Knight, D.W.; Allemann, R.K.
6- and 14-Fluoro farnesyl diphosphate: mechanistic probes for the reaction catalysed by aristolochene synthase
Org. Biomol. Chem.
7
962-975
2009
Penicillium roqueforti
Faraldos, J.A.; Antonczak, A.K.; Gonzalez, V.; Fullerton, R.; Tippmann, E.M.; Allemann, R.K.
Probing eudesmane cation-pi interactions in catalysis by aristolochene synthase with non-canonical amino acids
J. Am. Chem. Soc.
133
13906-13909
2011
Penicillium roqueforti
Faraldos, J.A.; Gonzalez, V.; Senske, M.; Allemann, R.K.
Templating effects in aristolochene synthase catalysis: elimination versus cyclisation
Org. Biomol. Chem.
9
6920-6923
2011
Penicillium roqueforti (Q03471), Penicillium roqueforti
Faraldos, J.A.; Allemann, R.K.
Inhibition of (+)-aristolochene synthase with iminium salts resembling eudesmane cation
Org. Lett.
13
1202-1205
2011
Penicillium roqueforti (Q03471)
Chen, M.; Al-lami, N.; Janvier, M.; DAntonio, E.L.; Faraldos, J.A.; Cane, D.E.; Allemann, R.K.; Christianson, D.W.
Mechanistic insights from the binding of substrate and carbocation intermediate analogues to aristolochene synthase
Biochemistry
52
5441-5453
2013
Aspergillus terreus (Q9UR08), Aspergillus terreus
van der Kamp, M.W.; Sirirak, J.; ?urek, J.; Allemann, R.K.; Mulholland, A.J.
Conformational change and ligand binding in the aristolochene synthase catalytic cycle
Biochemistry
52
8094-8105
2013
Aspergillus terreus (Q9UR08)
Faraldos, J.A.; Gonzalez, V.; Allemann, R.K.
The role of aristolochene synthase in diphosphate activation
Chem. Commun. (Camb. )
48
3230-3232
2012
Penicillium roqueforti (Q03471), Penicillium roqueforti
Rising, K.A.; Crenshaw, C.M.; Koo, H.J.; Subramanian, T.; Chehade, K.A.; Starks, C.; Allen, K.D.; Andres, D.A.; Spielmann, H.P.; Noel, J.P.; Chappell, J.
Formation of a novel macrocyclic alkaloid from the unnatural farnesyl diphosphate analogue anilinogeranyl diphosphate by 5-epi-aristolochene synthase
ACS Chem. Biol.
10
1729-1736
2015
Nicotiana tabacum (Q40577), Nicotiana tabacum
Chen, M.; Chou, W.K.; Al-Lami, N.; Faraldos, J.A.; Allemann, R.K.; Cane, D.E.; Christianson, D.W.
Probing the role of active site water in the sesquiterpene cyclization reaction catalyzed by aristolochene synthase
Biochemistry
55
2864-2874
2016
Aspergillus terreus (Q9UR08)
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