BRENDA - Enzyme Database
show all sequences of 4.2.3.9

Probing the role of active site water in the sesquiterpene cyclization reaction catalyzed by aristolochene synthase

Chen, M.; Chou, W.K.; Al-Lami, N.; Faraldos, J.A.; Allemann, R.K.; Cane, D.E.; Christianson, D.W.; Biochemistry 55, 2864-2874 (2016)

Data extracted from this reference:

Crystallization (Commentary)
Crystallization
Organism
wild type and mutant enzymes in complex with (2E,6E)-farnesyl diphosphate or 4, sitting drop vapor diffusion method, using 20% PEG 3350 as precipitant
Aspergillus terreus
Engineering
Amino acid exchange
Commentary
Organism
N299A
the mutation has decreasing effects on catalysis but significant effects on sesquiterpene product distributions of 50% germacrene A and 50% aristolochene
Aspergillus terreus
N299A/S303A
the decreasing have modest effects on catalysis but significant effects on sesquiterpene product distributions with germacrene A as main product and (E)-nerolidol and aristolochene as by-products
Aspergillus terreus
N299L
the mutation has decreasing effects on sesquiterpene product distributions with germacrene A and aristolochene as main product and (E)-nerolidol as by-product
Aspergillus terreus
N299V
inactive
Aspergillus terreus
Q151E
the mutation has decreasing effects on catalysis but significant effects on sesquiterpene product distributions with aristolochene and germacrene A as main products, and (E)-nerolidol and (E,E)-farnesol as by-products
Aspergillus terreus
Q151H
the mutation has decreasing effects on catalysis but significant effects on sesquiterpene product distributions with germacrene A and (E,E)-farnesol as main products and (E)-nerolidol and aristolochene as by-products
Aspergillus terreus
S303A
the mutation has increasing effects on catalysis and significant effects on sesquiterpene product distributions with germacrene A and (E)-nerolidol as by-products
Aspergillus terreus
S303D
the mutation has decreasing effects on catalysis but significant effects on sesquiterpene product distributions with germacrene A and (E,E)-farnesol as main products and (E)-nerolidol and aristolochene as by-products
Aspergillus terreus
S303H
the mutation has decreasing effects on catalysis but significant effects on sesquiterpene product distributions with germacrene A as main product and (E,E)-farnesol, (E)-nerolidol and aristolochene as by-products
Aspergillus terreus
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.000042
-
(2E,6E)-farnesyl diphosphate
mutant enzyme Q151H, at pH 8.0 and 30C
Aspergillus terreus
0.000061
-
(2E,6E)-farnesyl diphosphate
mutant enzyme S303H, at pH 8.0 and 30C
Aspergillus terreus
0.000099
-
(2E,6E)-farnesyl diphosphate
wild type enzyme, at pH 8.0 and 30C
Aspergillus terreus
0.0001
-
(2E,6E)-farnesyl diphosphate
mutant enzyme Q151E, at pH 8.0 and 30C
Aspergillus terreus
0.00012
-
(2E,6E)-farnesyl diphosphate
mutant enzyme S303A, at pH 8.0 and 30C
Aspergillus terreus
0.00036
-
(2E,6E)-farnesyl diphosphate
mutant enzyme S303D, at pH 8.0 and 30C
Aspergillus terreus
0.00041
-
(2E,6E)-farnesyl diphosphate
mutant enzyme N299A, at pH 8.0 and 30C; mutant enzyme N299A/S303A, at pH 8.0 and 30C
Aspergillus terreus
Metals/Ions
Metals/Ions
Commentary
Organism
Structure
Mg2+
required
Aspergillus terreus
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
(2E,6E)-farnesyl diphosphate
Aspergillus terreus
-
aristolochene + diphosphate
-
-
?
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Aspergillus terreus
Q9UR08
-
-
Purification (Commentary)
Commentary
Organism
Ni-NTA column chromatography, HiTrap Q column chromatography, and Superdex 26/60 gel filtration
Aspergillus terreus
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(2E,6E)-farnesyl diphosphate
-
747103
Aspergillus terreus
aristolochene + diphosphate
-
-
-
?
additional information
no activity with farnesyl S-thiolodiphosphate
747103
Aspergillus terreus
?
-
-
-
-
Turnover Number [1/s]
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
0.00041
-
(2E,6E)-farnesyl diphosphate
mutant enzyme S303D, at pH 8.0 and 30C
Aspergillus terreus
0.00063
-
(2E,6E)-farnesyl diphosphate
mutant enzyme Q151H, at pH 8.0 and 30C
Aspergillus terreus
0.0013
-
(2E,6E)-farnesyl diphosphate
mutant enzyme S303H, at pH 8.0 and 30C
Aspergillus terreus
0.0015
-
(2E,6E)-farnesyl diphosphate
mutant enzyme Q151E, at pH 8.0 and 30C
Aspergillus terreus
0.0058
-
(2E,6E)-farnesyl diphosphate
mutant enzyme N299A/S303A, at pH 8.0 and 30C
Aspergillus terreus
0.012
-
(2E,6E)-farnesyl diphosphate
mutant enzyme N299A, at pH 8.0 and 30C
Aspergillus terreus
0.027
-
(2E,6E)-farnesyl diphosphate
wild type enzyme, at pH 8.0 and 30C
Aspergillus terreus
0.045
-
(2E,6E)-farnesyl diphosphate
mutant enzyme S303A, at pH 8.0 and 30C
Aspergillus terreus
Crystallization (Commentary) (protein specific)
Crystallization
Organism
wild type and mutant enzymes in complex with (2E,6E)-farnesyl diphosphate or 4, sitting drop vapor diffusion method, using 20% PEG 3350 as precipitant
Aspergillus terreus
Engineering (protein specific)
Amino acid exchange
Commentary
Organism
N299A
the mutation has decreasing effects on catalysis but significant effects on sesquiterpene product distributions of 50% germacrene A and 50% aristolochene
Aspergillus terreus
N299A/S303A
the decreasing have modest effects on catalysis but significant effects on sesquiterpene product distributions with germacrene A as main product and (E)-nerolidol and aristolochene as by-products
Aspergillus terreus
N299L
the mutation has decreasing effects on sesquiterpene product distributions with germacrene A and aristolochene as main product and (E)-nerolidol as by-product
Aspergillus terreus
N299V
inactive
Aspergillus terreus
Q151E
the mutation has decreasing effects on catalysis but significant effects on sesquiterpene product distributions with aristolochene and germacrene A as main products, and (E)-nerolidol and (E,E)-farnesol as by-products
Aspergillus terreus
Q151H
the mutation has decreasing effects on catalysis but significant effects on sesquiterpene product distributions with germacrene A and (E,E)-farnesol as main products and (E)-nerolidol and aristolochene as by-products
Aspergillus terreus
S303A
the mutation has increasing effects on catalysis and significant effects on sesquiterpene product distributions with germacrene A and (E)-nerolidol as by-products
Aspergillus terreus
S303D
the mutation has decreasing effects on catalysis but significant effects on sesquiterpene product distributions with germacrene A and (E,E)-farnesol as main products and (E)-nerolidol and aristolochene as by-products
Aspergillus terreus
S303H
the mutation has decreasing effects on catalysis but significant effects on sesquiterpene product distributions with germacrene A as main product and (E,E)-farnesol, (E)-nerolidol and aristolochene as by-products
Aspergillus terreus
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.000042
-
(2E,6E)-farnesyl diphosphate
mutant enzyme Q151H, at pH 8.0 and 30C
Aspergillus terreus
0.000061
-
(2E,6E)-farnesyl diphosphate
mutant enzyme S303H, at pH 8.0 and 30C
Aspergillus terreus
0.000099
-
(2E,6E)-farnesyl diphosphate
wild type enzyme, at pH 8.0 and 30C
Aspergillus terreus
0.0001
-
(2E,6E)-farnesyl diphosphate
mutant enzyme Q151E, at pH 8.0 and 30C
Aspergillus terreus
0.00012
-
(2E,6E)-farnesyl diphosphate
mutant enzyme S303A, at pH 8.0 and 30C
Aspergillus terreus
0.00036
-
(2E,6E)-farnesyl diphosphate
mutant enzyme S303D, at pH 8.0 and 30C
Aspergillus terreus
0.00041
-
(2E,6E)-farnesyl diphosphate
mutant enzyme N299A, at pH 8.0 and 30C; mutant enzyme N299A/S303A, at pH 8.0 and 30C
Aspergillus terreus
Metals/Ions (protein specific)
Metals/Ions
Commentary
Organism
Structure
Mg2+
required
Aspergillus terreus
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
(2E,6E)-farnesyl diphosphate
Aspergillus terreus
-
aristolochene + diphosphate
-
-
?
Purification (Commentary) (protein specific)
Commentary
Organism
Ni-NTA column chromatography, HiTrap Q column chromatography, and Superdex 26/60 gel filtration
Aspergillus terreus
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(2E,6E)-farnesyl diphosphate
-
747103
Aspergillus terreus
aristolochene + diphosphate
-
-
-
?
additional information
no activity with farnesyl S-thiolodiphosphate
747103
Aspergillus terreus
?
-
-
-
-
Turnover Number [1/s] (protein specific)
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
0.00041
-
(2E,6E)-farnesyl diphosphate
mutant enzyme S303D, at pH 8.0 and 30C
Aspergillus terreus
0.00063
-
(2E,6E)-farnesyl diphosphate
mutant enzyme Q151H, at pH 8.0 and 30C
Aspergillus terreus
0.0013
-
(2E,6E)-farnesyl diphosphate
mutant enzyme S303H, at pH 8.0 and 30C
Aspergillus terreus
0.0015
-
(2E,6E)-farnesyl diphosphate
mutant enzyme Q151E, at pH 8.0 and 30C
Aspergillus terreus
0.0058
-
(2E,6E)-farnesyl diphosphate
mutant enzyme N299A/S303A, at pH 8.0 and 30C
Aspergillus terreus
0.012
-
(2E,6E)-farnesyl diphosphate
mutant enzyme N299A, at pH 8.0 and 30C
Aspergillus terreus
0.027
-
(2E,6E)-farnesyl diphosphate
wild type enzyme, at pH 8.0 and 30C
Aspergillus terreus
0.045
-
(2E,6E)-farnesyl diphosphate
mutant enzyme S303A, at pH 8.0 and 30C
Aspergillus terreus
KCat/KM [mM/s]
kcat/KM Value [1/mMs-1]
kcat/KM Value Maximum [1/mMs-1]
Substrate
Commentary
Organism
Structure
1.1
-
(2E,6E)-farnesyl diphosphate
mutant enzyme S303D, at pH 8.0 and 30C
Aspergillus terreus
14
-
(2E,6E)-farnesyl diphosphate
mutant enzyme N299A/S303A, at pH 8.0 and 30C
Aspergillus terreus
15
-
(2E,6E)-farnesyl diphosphate
mutant enzyme Q151E, at pH 8.0 and 30C; mutant enzyme Q151H, at pH 8.0 and 30C
Aspergillus terreus
21
-
(2E,6E)-farnesyl diphosphate
mutant enzyme S303H, at pH 8.0 and 30C
Aspergillus terreus
29
-
(2E,6E)-farnesyl diphosphate
mutant enzyme N299A, at pH 8.0 and 30C
Aspergillus terreus
270
-
(2E,6E)-farnesyl diphosphate
wild type enzyme, at pH 8.0 and 30C
Aspergillus terreus
370
-
(2E,6E)-farnesyl diphosphate
mutant enzyme S303A, at pH 8.0 and 30C
Aspergillus terreus
KCat/KM [mM/s] (protein specific)
KCat/KM Value [1/mMs-1]
KCat/KM Value Maximum [1/mMs-1]
Substrate
Commentary
Organism
Structure
1.1
-
(2E,6E)-farnesyl diphosphate
mutant enzyme S303D, at pH 8.0 and 30C
Aspergillus terreus
14
-
(2E,6E)-farnesyl diphosphate
mutant enzyme N299A/S303A, at pH 8.0 and 30C
Aspergillus terreus
15
-
(2E,6E)-farnesyl diphosphate
mutant enzyme Q151E, at pH 8.0 and 30C; mutant enzyme Q151H, at pH 8.0 and 30C
Aspergillus terreus
21
-
(2E,6E)-farnesyl diphosphate
mutant enzyme S303H, at pH 8.0 and 30C
Aspergillus terreus
29
-
(2E,6E)-farnesyl diphosphate
mutant enzyme N299A, at pH 8.0 and 30C
Aspergillus terreus
270
-
(2E,6E)-farnesyl diphosphate
wild type enzyme, at pH 8.0 and 30C
Aspergillus terreus
370
-
(2E,6E)-farnesyl diphosphate
mutant enzyme S303A, at pH 8.0 and 30C
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
-
-
-
1
9
-
-
7
-
1
-
1
-
1
-
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1
-
-
-
-
-
2
-
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-
8
-
-
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-
-
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1
9
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7
-
1
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1
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1
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-
-
2
-
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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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2
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1
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1
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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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1
2
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1
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2
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1
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2
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1
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1
2
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1
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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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9
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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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2
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5
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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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2
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1
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9
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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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2
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1
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2
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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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1
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2
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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2
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1
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679187
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664584
Forcat
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665301
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644241
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Tyrosine 92 of aristolochene s ...
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Germacrene A is a product of t ...
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644244
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Aristolochene synthase. Isolat ...
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Aristolochene biosynthesis. St ...
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Aristolochene biosynthesis and ...
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Hohn
Purification and characterizat ...
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