BRENDA - Enzyme Database
show all sequences of 5.4.99.39

beta-Amyrin synthase from Euphorbia tirucalli. Steric bulk, not the Pi-electrons of Phe, at position 474 has a key role in affording the correct folding of the substrate to complete the normal polycyclization cascade

Ito, R.; Masukawa, Y.; Nakada, C.; Amari, K.; Nakano, C.; Hoshino, T.; Org. Biomol. Chem. 12, 3836-3846 (2014)

Data extracted from this reference:

Cloned(Commentary)
Cloned (Commentary)
Organism
recombinant expression of wild-type and mutant enzymes in Saccharomyces cerevisiae strain GIL77
Euphorbia tirucalli
Engineering
Protein Variants
Commentary
Organism
F474A
site-directed mutagenesis, the mutant produces significantly larger amounts of the bicyclic products and a decreased amount of beta-amyrin compared to wild-type. The mutant variant produces (9betaH)-polypoda-7,13,17,21-tetraen-3beta-ol and (9betaH)-polypoda-8(26),13,17,21-tetraen-3beta-ol, which are generated from a chair-boat folding conformation
Euphorbia tirucalli
F474G
site-directed mutagenesis, the mutant produces significantly larger amounts of the bicyclic products and a decreased amount of beta-amyrin compared to wild-type
Euphorbia tirucalli
F474H
site-directed mutagenesis
Euphorbia tirucalli
F474L
site-directed mutagenesis, the mutant shows a significantly decreased production of bicyclic compounds, and in turn exhibits a higher production of beta-amyrin compared to wild-type
Euphorbia tirucalli
F474M
site-directed mutagenesis, the mutant shows a significantly decreased production of bicyclic compounds, and in turn exhibits a higher production of beta-amyrin compared to wild-type
Euphorbia tirucalli
F474T
site-directed mutagenesis
Euphorbia tirucalli
F474V
site-directed mutagenesis, the mutant shows a significantly decreased production of bicyclic compounds, and in turn exhibits a higher production of beta-amyrin compared to wild-type
Euphorbia tirucalli
F474W
site-directed mutagenesis
Euphorbia tirucalli
F474Y
site-directed mutagenesis
Euphorbia tirucalli
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
(3S)-2,3-epoxy-2,3-dihydrosqualene
Euphorbia tirucalli
-
beta-amyrin
-
-
r
Organism
Organism
UniProt
Commentary
Textmining
Euphorbia tirucalli
Q401R6
-
-
Reaction
Reaction
Commentary
Organism
Reaction ID
(3S)-2,3-epoxy-2,3-dihydrosqualene = beta-amyrin
cyclization pathway of (3S)-2,3-oxidosqualene to generate beta-amyrin triterpene via bicyclic, malabaricanyl, dammarenyl, baccharenyl, lupanyl, and oleanyl cation intermediates, detailed mechanism overview
Euphorbia tirucalli
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
Substrate Product ID
(3S)-2,3-epoxy-2,3-dihydrosqualene
-
748805
Euphorbia tirucalli
beta-amyrin
-
-
-
r
additional information
GC-MS and NMR spectroscopic product and metabolites identification from reactions of wild-type and mutant enzymes, overview
748805
Euphorbia tirucalli
?
-
-
-
-
Synonyms
Synonyms
Commentary
Organism
beta-amyrin cyclase
-
Euphorbia tirucalli
EtAS
-
Euphorbia tirucalli
Cloned(Commentary) (protein specific)
Commentary
Organism
recombinant expression of wild-type and mutant enzymes in Saccharomyces cerevisiae strain GIL77
Euphorbia tirucalli
Engineering (protein specific)
Protein Variants
Commentary
Organism
F474A
site-directed mutagenesis, the mutant produces significantly larger amounts of the bicyclic products and a decreased amount of beta-amyrin compared to wild-type. The mutant variant produces (9betaH)-polypoda-7,13,17,21-tetraen-3beta-ol and (9betaH)-polypoda-8(26),13,17,21-tetraen-3beta-ol, which are generated from a chair-boat folding conformation
Euphorbia tirucalli
F474G
site-directed mutagenesis, the mutant produces significantly larger amounts of the bicyclic products and a decreased amount of beta-amyrin compared to wild-type
Euphorbia tirucalli
F474H
site-directed mutagenesis
Euphorbia tirucalli
F474L
site-directed mutagenesis, the mutant shows a significantly decreased production of bicyclic compounds, and in turn exhibits a higher production of beta-amyrin compared to wild-type
Euphorbia tirucalli
F474M
site-directed mutagenesis, the mutant shows a significantly decreased production of bicyclic compounds, and in turn exhibits a higher production of beta-amyrin compared to wild-type
Euphorbia tirucalli
F474T
site-directed mutagenesis
Euphorbia tirucalli
F474V
site-directed mutagenesis, the mutant shows a significantly decreased production of bicyclic compounds, and in turn exhibits a higher production of beta-amyrin compared to wild-type
Euphorbia tirucalli
F474W
site-directed mutagenesis
Euphorbia tirucalli
F474Y
site-directed mutagenesis
Euphorbia tirucalli
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
(3S)-2,3-epoxy-2,3-dihydrosqualene
Euphorbia tirucalli
-
beta-amyrin
-
-
r
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
ID
(3S)-2,3-epoxy-2,3-dihydrosqualene
-
748805
Euphorbia tirucalli
beta-amyrin
-
-
-
r
additional information
GC-MS and NMR spectroscopic product and metabolites identification from reactions of wild-type and mutant enzymes, overview
748805
Euphorbia tirucalli
?
-
-
-
-
General Information
General Information
Commentary
Organism
evolution
residue F474 of Euphorbia tirucalli beta-amyrin cyclase is highly conserved in the superfamily of oxidosqualene cyclases
Euphorbia tirucalli
malfunction
enzyme mutant F474A and F474G produces significantly larger amounts of the bicyclic products and a decreased amount of beta-amyrin compared to wild-type. The mutant variant F474A produces (9betaH)-polypoda-7,13,17,21-tetraen-3beta-ol and (9betaH)-polypoda-8(26),13,17,21-tetraen-3beta-ol, which are generated from a chair-boat folding conformation. Substitutions with aliphatic amino acids lacking Pi-electrons such as Val, Leu, and Met lead to a significantly decreased production of bicyclic compounds, and in turn exhibit a higher production of beta-amyrin
Euphorbia tirucalli
additional information
catalytically important residue F474 residue is located near the B-ring formation site. The major role of Phe474 is not to stabilize the transient cation via cation-Pi interaction, but is to confer the appropriate steric bulk near the B-ring formation site, leading to the completion of the normal polycyclization pathway without accumulation of abortive cyclization products
Euphorbia tirucalli
General Information (protein specific)
General Information
Commentary
Organism
evolution
residue F474 of Euphorbia tirucalli beta-amyrin cyclase is highly conserved in the superfamily of oxidosqualene cyclases
Euphorbia tirucalli
malfunction
enzyme mutant F474A and F474G produces significantly larger amounts of the bicyclic products and a decreased amount of beta-amyrin compared to wild-type. The mutant variant F474A produces (9betaH)-polypoda-7,13,17,21-tetraen-3beta-ol and (9betaH)-polypoda-8(26),13,17,21-tetraen-3beta-ol, which are generated from a chair-boat folding conformation. Substitutions with aliphatic amino acids lacking Pi-electrons such as Val, Leu, and Met lead to a significantly decreased production of bicyclic compounds, and in turn exhibit a higher production of beta-amyrin
Euphorbia tirucalli
additional information
catalytically important residue F474 residue is located near the B-ring formation site. The major role of Phe474 is not to stabilize the transient cation via cation-Pi interaction, but is to confer the appropriate steric bulk near the B-ring formation site, leading to the completion of the normal polycyclization pathway without accumulation of abortive cyclization products
Euphorbia tirucalli
Other publictions for EC 5.4.99.39
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
Synonyms
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)
748823
Ma
-
beta-Amyrin synthase, one of ...
Artemisia annua, Avena longiglumis, Barbarea vurlgaris, Bupleurum chinense, Euphorbia tirucalli, Glycine max, Glycyrrhiza uralensis, Gypsophila vaccaria, Medicago truncatula, Panax japonicus, Panax quinquefolius, Polygala tenuifolia
Pak. J. Bot.
50
231-243
2018
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12
11
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11
1
39
39
1
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746004
Jo
beta-Amyrin synthase (EsBAS) ...
Eleutherococcus senticosus
Phytochemistry
135
53-63
2017
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1
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1
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7
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5
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2
1
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5
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1
2
2
1
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747546
Hoshino
Euphorbia tirucalli beta-amyr ...
Euphorbia tirucalli
ChemBioChem
18
2145-2155
2017
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1
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18
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1
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1
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1
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18
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1
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1
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1
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2
2
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747786
Sun
beta-Amyrin synthase from Con ...
Eschenbachia blinii
FEBS open bio
7
1575-1585
2017
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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
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747921
Um
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Functional characterization o ...
Platycodon grandiflorus
Hortic. Environ. Biotechnol.
58
613-619
2017
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748812
Ito
beta-Amyrin synthase from Eup ...
Euphorbia tirucalli
Org. Biomol. Chem.
15
177-188
2017
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1
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15
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2
2
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748772
Andre
Multifunctional oxidosqualene ...
Malus domestica
New Phytol.
211
1279-1294
2016
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1
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3
3
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749323
Liu
An intronless beta-amyrin syn ...
Gentiana straminea
Sci. Rep.
6
33364
2016
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1
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5
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4
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8
4
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730595
Jin
Isolation and characterization ...
Polygala tenuifolia
Plant Cell Rep.
33
511-519
2014
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730640
Misra
Methyl jasmonate-elicited tran ...
Ocimum basilicum
Plant Physiol.
164
1028-1044
2014
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747597
Liu
-
Cloning, prokaryotic expressi ...
Psammosilene tunicoides
Chin. Tradit. Herbal Drugs
45
1456-1460
2014
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748805
Ito
beta-Amyrin synthase from Eup ...
Euphorbia tirucalli
Org. Biomol. Chem.
12
3836-3846
2014
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1
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729601
Ito
Effect of cation-pi interactio ...
Euphorbia tirucalli
Chemistry
19
17150-17158
2013
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729707
Ito
Purification, kinetics, inhibi ...
Euphorbia tirucalli
FEBS J.
280
1267-1280
2013
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730571
Yu
Functional characterization of ...
Catharanthus roseus
Phytochemistry
91
122-127
2013
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711990
Brendolise
An unusual plant triterpene sy ...
Malus domestica
FEBS J.
278
2485-2499
2011
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715030
Sawai
Molecular characterization of ...
Aster tataricus
FEBS Lett.
585
1031-1036
2011
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716502
Takagi
Manipulation of saponin biosyn ...
Glycine max
Plant Cell Rep.
30
1835-1846
2011
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Two oxidosqualene cyclases res ...
Solanum lycopersicum
Plant Physiol.
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2011
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716192
Yendo
Production of plant bioactive ...
Aster sedifolius, Centella asiatica, Gentiana straminea, Gypsophila vaccaria, Medicago truncatula, Panax ginseng
Mol. Biotechnol.
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2010
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716908
Shabani
-
Assessment of squalene synthas ...
Glycyrrhiza glabra
Russ. J. Plant Physiol.
57
480-484
2010
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694622
Confalonieri
Enhanced triterpene saponin bi ...
Aster sedifolius
Plant Biotechnol. J.
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172-182
2009
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694752
Shibuya
Identification of a product sp ...
Arabidopsis thaliana
Plant Physiol. Biochem.
47
26-30
2009
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683463
Kirby
Engineering triterpene product ...
Artemisia annua
FEBS J.
275
1852-1859
2008
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694761
Cammareri
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Molecular characterization of ...
Aster sedifolius
Plant Sci.
175
255-261
2008
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683462
Basyuni
Triterpene synthases from the ...
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FEBS J.
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5028-5042
2007
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683985
Meesapyodsuk
Saponin biosynthesis in Sapona ...
Gypsophila vaccaria
Plant Physiol.
143
959-969
2007
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684059
Chung
-
Molecular characterization of ...
Glycine max
Russ. J. Plant Physiol.
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518-523
2007
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682450
Sawai
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Functional and structural anal ...
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Plant Sci.
170
247-257
2006
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683972
Kajikawa
Cloning and characterization o ...
Euphorbia tirucalli
Phytochemistry
66
1759-1766
2005
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683583
Abe
Enzymatic cyclization of 22,23 ...
Pisum sativum
J. Am. Chem. Soc.
126
3426-3427
2004
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683584
Abe
Mechanism and stereochemistry ...
Pisum sativum
J. Am. Chem. Soc.
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6880-6881
2004
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684074
Noma
-
Enzymatic formation of an unna ...
Pisum sativum
Tetrahedron Lett.
45
8299-8301
2004
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683215
Zhang
Oxidosqualene cyclases from ce ...
Betula platyphylla
Biol. Pharm. Bull.
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642-650
2003
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683984
Iturbe-Ormaetxe
Molecular cloning and characte ...
Medicago truncatula
Plant Mol. Biol.
51
731-743
2003
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683214
Hayashi
Cloning and characterization o ...
Glycyrrhiza glabra
Biol. Pharm. Bull.
24
912-916
2001
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4
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683422
Morita
Molecular cloning and function ...
Pisum sativum
Eur. J. Biochem.
267
3453-3460
2000
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683581
Kushiro
-
Mutational studies on triterpe ...
Panax ginseng
J. Am. Chem. Soc.
122
6816-6824
2000
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4
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683580
Kushiro
-
Chimeric triterpene synthase. ...
Arabidopsis thaliana
J. Am. Chem. Soc.
121
1208-1216
1999
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1
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683420
Kushiro
beta-Amyrin synthase - cloning ...
Panax ginseng
Eur. J. Biochem.
256
238-244
1998
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683970
Taton
-
Inhibition of higher plant 2,3 ...
Pisum sativum
Phytochemistry
43
75-81
1996
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3
1
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