BRENDA - Enzyme Database
show all sequences of 4.2.3.9

X-ray crystallographic studies of substrate binding to aristolochene synthase suggest a metal ion binding sequence for catalysis

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.; J. Biol. Chem. 283, 15431-15439 (2008)

Data extracted from this reference:

Cloned(Commentary)
Commentary
Organism
recombinant aristolochene synthase is expressed in Escherichia coli BL21(DE3)pLysS
Aspergillus terreus
Crystallization (Commentary)
Crystallization
Organism
crystallization by the hanging drop, vapor diffusion method at 4°C, the crystal structure determined from crystals soaked with farnesyl diphosphate reveals the binding of intact farnesyl diphosphate to monomers A-C, and the binding of diphosphate anion and Mg2+ to monomer D. The structure of the complex with 2-fluorofarnesyl diphosphate reveals 2-fluorofarnesyl diphosphate binding to all subunits of the tetramer, with Mg2+B accompanying the binding of this analogue only in monomer D. The structure of the complex with 12,13-difluorofarnesyl diphosphate reveals the binding of intact 12,13-difluorofarnesyl diphosphate to monomers A-C in the open conformation and the binding of diphosphate anion, Mg2+B, and Mg2+C to monomer D in a predominantly closed conformation
Aspergillus terreus
Inhibitors
Inhibitors
Commentary
Organism
Structure
12,13-difluorofarnesyl diphosphate
incubation of 12,13-difluorofarnesyl diphosphate with for 30 h does not generate any pentane-extractable products based on GC-MS analysis
Aspergillus terreus
Metals/Ions
Metals/Ions
Commentary
Organism
Structure
Mg2+
enzyme utilizes a trinuclear magnesium cluster to trigger the departure of the diphosphate leaving group, thereby forming an allylic carbocation that typically reacts with one of the remaining sigma-bonds of the substrate
Aspergillus terreus
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
farnesyl diphosphate
Aspergillus terreus
The universal sesquiterpene precursor farnesyl diphosphate (15-carbon isoprenoid) is cyclized in an Mg2-dependent reaction to form the bicyclic hydrocarbon aristolochene and a diphosphate anion coproduct
(+)-aristolochene + diphosphate
-
-
?
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Aspergillus terreus
Q9UR08
-
-
Purification (Commentary)
Commentary
Organism
-
Aspergillus terreus
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
2-fluorofarnesyl diphosphate
two products are identified in a 95/5 ratio by GS-MS
693062
Aspergillus terreus
2-fluorogermacrene A
-
-
-
?
farnesyl diphosphate
The universal sesquiterpene precursor farnesyl diphosphate (15-carbon isoprenoid) is cyclized in an Mg2-dependent reaction to form the bicyclic hydrocarbon aristolochene and a diphosphate anion coproduct
693062
Aspergillus terreus
(+)-aristolochene + diphosphate
-
-
-
?
Subunits
Subunits
Commentary
Organism
dimer
in solution
Aspergillus terreus
tetramer
crystal structure
Aspergillus terreus
Temperature Optimum [°C]
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
30
-
assay at
Aspergillus terreus
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.6
-
assay at
Aspergillus terreus
Cloned(Commentary) (protein specific)
Commentary
Organism
recombinant aristolochene synthase is expressed in Escherichia coli BL21(DE3)pLysS
Aspergillus terreus
Crystallization (Commentary) (protein specific)
Crystallization
Organism
crystallization by the hanging drop, vapor diffusion method at 4°C, the crystal structure determined from crystals soaked with farnesyl diphosphate reveals the binding of intact farnesyl diphosphate to monomers A-C, and the binding of diphosphate anion and Mg2+ to monomer D. The structure of the complex with 2-fluorofarnesyl diphosphate reveals 2-fluorofarnesyl diphosphate binding to all subunits of the tetramer, with Mg2+B accompanying the binding of this analogue only in monomer D. The structure of the complex with 12,13-difluorofarnesyl diphosphate reveals the binding of intact 12,13-difluorofarnesyl diphosphate to monomers A-C in the open conformation and the binding of diphosphate anion, Mg2+B, and Mg2+C to monomer D in a predominantly closed conformation
Aspergillus terreus
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
12,13-difluorofarnesyl diphosphate
incubation of 12,13-difluorofarnesyl diphosphate with for 30 h does not generate any pentane-extractable products based on GC-MS analysis
Aspergillus terreus
Metals/Ions (protein specific)
Metals/Ions
Commentary
Organism
Structure
Mg2+
enzyme utilizes a trinuclear magnesium cluster to trigger the departure of the diphosphate leaving group, thereby forming an allylic carbocation that typically reacts with one of the remaining sigma-bonds of the substrate
Aspergillus terreus
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
farnesyl diphosphate
Aspergillus terreus
The universal sesquiterpene precursor farnesyl diphosphate (15-carbon isoprenoid) is cyclized in an Mg2-dependent reaction to form the bicyclic hydrocarbon aristolochene and a diphosphate anion coproduct
(+)-aristolochene + diphosphate
-
-
?
Purification (Commentary) (protein specific)
Commentary
Organism
-
Aspergillus terreus
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
2-fluorofarnesyl diphosphate
two products are identified in a 95/5 ratio by GS-MS
693062
Aspergillus terreus
2-fluorogermacrene A
-
-
-
?
farnesyl diphosphate
The universal sesquiterpene precursor farnesyl diphosphate (15-carbon isoprenoid) is cyclized in an Mg2-dependent reaction to form the bicyclic hydrocarbon aristolochene and a diphosphate anion coproduct
693062
Aspergillus terreus
(+)-aristolochene + diphosphate
-
-
-
?
Subunits (protein specific)
Subunits
Commentary
Organism
dimer
in solution
Aspergillus terreus
tetramer
crystal structure
Aspergillus terreus
Temperature Optimum [°C] (protein specific)
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
30
-
assay at
Aspergillus terreus
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.6
-
assay at
Aspergillus terreus
Other publictions for EC 4.2.3.9
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [°C]
Temperature Range [°C]
Temperature Stability [°C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [°C] (protein specific)
Temperature Range [°C] (protein specific)
Temperature Stability [°C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
747103
Chen
Probing the role of active si ...
Aspergillus terreus
Biochemistry
55
2864-2874
2016
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1
9
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7
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1
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8
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7
7
747509
Faraldos
Enzymatic synthesis of natura ...
Penicillium roqueforti
Chem. Commun. (Camb.)
52
14027-14030
2016
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746589
Rising
Formation of a novel macrocyc ...
Nicotiana tabacum
ACS Chem. Biol.
10
1729-1736
2015
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1
1
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2
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2
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729236
Chen
Mechanistic insights from the ...
Aspergillus terreus
Biochemistry
52
5441-5453
2013
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1
1
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729242
van der Kamp
Conformational change and liga ...
Aspergillus terreus
Biochemistry
52
8094-8105
2013
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1
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1
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729580
Faraldos
The role of aristolochene synt ...
Penicillium roqueforti
Chem. Commun. (Camb. )
48
3230-3232
2012
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9
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7
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1
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7
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7
7
715288
Faraldos
Probing eudesmane cation-pi in ...
Penicillium roqueforti
J. Am. Chem. Soc.
133
13906-13909
2011
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1
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5
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5
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1
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5
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5
5
716415
Faraldos
Templating effects in aristolo ...
Penicillium roqueforti
Org. Biomol. Chem.
9
6920-6923
2011
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8
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9
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1
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9
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9
9
716419
Faraldos
Inhibition of (+)-aristolochen ...
Penicillium roqueforti
Org. Lett.
13
1202-1205
2011
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704204
Faraldos
Bisabolyl-derived sesquiterpen ...
Nicotiana tabacum
J. Am. Chem. Soc.
132
4281-4289
2010
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1
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1
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2
705304
Faraldos
Intermediacy of eudesmane cati ...
Penicillium roqueforti
J. Org. Chem.
75
1119-1125
2010
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1
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2
1
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1
1
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1
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1
1
706047
Miller
6- and 14-Fluoro farnesyl diph ...
Penicillium roqueforti
Org. Biomol. Chem.
7
962-975
2009
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691962
Christianson
Unearthing the roots of the te ...
Aspergillus terreus
Curr. Opin. Chem. Biol.
12
141-150
2008
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693062
Shishova
X-ray crystallographic studies ...
Aspergillus terreus
J. Biol. Chem.
283
15431-15439
2008
-
-
1
1
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1
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1
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1
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694515
Miller
Stereochemistry of eudesmane c ...
Penicillium roqueforti
Org. Biomol. Chem.
6
2346-2354
2008
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1
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678256
Shishova
X-ray crystal structure of ari ...
Aspergillus terreus
Biochemistry
46
1941-1951
2007
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1
1
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1
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3
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679187
Yu
Probing the reaction mechanism ...
Escherichia coli
Chem. Commun. (Camb. )
2007
4155-4157
2007
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679218
Miller
Aristolochene synthase-catalyz ...
Penicillium roqueforti
ChemBioChem
8
1819-1825
2007
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1
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1
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1
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1
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1
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680359
Allemann
Synthetic efficiency in enzyme ...
Penicillium roqueforti
J. Am. Chem. Soc.
129
13008-13013
2007
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1
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682226
Miller
Competitive inhibition of aris ...
Penicillium roqueforti
Org. Biomol. Chem.
5
3287-3298
2007
-
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3
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1
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1
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2
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1
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1
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1
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3
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3
3
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1
-
1
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1
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1
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1
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682223
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7
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8
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1
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1
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1
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1
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2
1
1
-
-
16
1
-
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-
1
-
-
7
-
-
-
-
8
-
1
-
1
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1
1
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-
-
2
1
1
-
-
16
1
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664584
Forcat
Dual role for phenylalanine 17 ...
Penicillium roqueforti
Chem. Commun. (Camb.)
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2094-2095
2004
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2
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2
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1
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1
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2
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2
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2
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-
1
-
-
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2
-
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665301
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Aristolochene synthase: mechan ...
Aspergillus terreus, Penicillium roqueforti
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7212-7221
2004
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16
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14
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4
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2
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12
-
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-
16
-
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-
14
-
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-
2
-
-
-
-
12
-
-
-
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644243
Deligeorgopoulou
Evidence for differential fold ...
Penicillium roqueforti
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7741-7747
2003
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1
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4
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5
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3
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1
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2
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5
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1
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6
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5
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1
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2
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5
-
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3
3
644241
Calvert
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Tyrosine 92 of aristolochene s ...
Penicillium roqueforti
Chem. Commun. (Camb.)
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2002
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1
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1
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1
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1
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1
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644242
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Germacrene A is a product of t ...
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2002
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1
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1
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2
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1
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1
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644240
Caruthers
Crystal structure determinatio ...
Penicillium roqueforti
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1
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1
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644244
Cane
Aristolochene synthase: purifi ...
Aspergillus terreus, Penicillium roqueforti
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354-364
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2
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3
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644239
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Purification and characterizat ...
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