Information on EC 5.4.99.39 - beta-amyrin synthase

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The expected taxonomic range for this enzyme is: Gunneridae

EC NUMBER
COMMENTARY hide
5.4.99.39
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RECOMMENDED NAME
GeneOntology No.
beta-amyrin synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(3S)-2,3-epoxy-2,3-dihydrosqualene = beta-amyrin
show the reaction diagram
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
avenacin biosynthesis, initial reactions
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Biosynthesis of secondary metabolites
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ginsenosides biosynthesis
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mangrove triterpenoid biosynthesis
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oleanolate biosynthesis
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pentacyclic triterpene biosynthesis
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Sesquiterpenoid and triterpenoid biosynthesis
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soybean saponin I biosynthesis
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superpathway avenacin A biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
(3S)-2,3-epoxy-2,3-dihydrosqualene mutase (cyclizing, beta-amyrin-forming)
Some organism possess a monofunctional beta-amyrin synthase [3,4,6-11], other have a multifunctional enzyme that also catalyses the synthesis of alpha-amyrin (EC 5.4.99.40) [5] or lupeol (EC 5.4.99.41) [6].
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
var. japonica
Uniprot
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
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saponin biosynthesis in soybean seeds is suppressed through RNA interference-mediated beta-amyrin synthase gene silencing
metabolism
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(3R)-2,2-dimethyl-3-[(3E,7E,11E)-3,7,12,16-tetramethylheptadeca-3,7,11,15-tetraen-1-yl]oxirane
(3alpha,9xi,10alpha)-4,4,14,20-tetramethylpregn-7-en-3-ol
show the reaction diagram
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pre-chair-chair-chair-boat conformation of substrate
about 1% of the yield with substrate 24,30-bisnor-2,3-oxidosqualene
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?
(3S)-2,3-epoxy-2,3-dihydrosqualene
beta-amyrin
show the reaction diagram
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isoform SITT1 produces 13% beta-amyrin
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?
(3S)-2,3-oxidosqualene
beta-amyrin
show the reaction diagram
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?
(S)-2,3-oxidosqualene
beta-amyrin
show the reaction diagram
2,3-oxidosqualene
beta-amyrin
show the reaction diagram
22,23-dihydro-2,3-oxidosqualene
euph-7-en-3beta-ol + bacchar-12-en-3beta-ol
show the reaction diagram
24,30-bisnor-2,3-oxidosqualene
29,30-bisnor-beta-amyrin + 29,30-bisnorgermanicol + 29,30-bisnor-delta-amyrin
show the reaction diagram
additional information
?
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enzyme is involved in saponin biosynthesis
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(S)-2,3-oxidosqualene
beta-amyrin
show the reaction diagram
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?
additional information
?
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enzyme is involved in saponin biosynthesis
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(4-bromophenyl)[2-fluoro-4-([6-[methyl(prop-2-en-1-yl)amino]hexyl]oxy)phenyl]methanone
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10-aza-10,11-dihydro-2,3-oxidosqualene
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19-aza-18,19,22,23-tetrahydro-2,3-oxidosqualene
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23-aza-22,23-dihydro-2,3-oxidosqualene
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Iminosqualene
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N,N-diethyl-2-[[(3beta)-17-methylideneandrost-5-en-3-yl]oxy]ethanamine
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Triton X-100
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at 0.05% highest activity of the enzyme
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.125
(3S)-2,2-dimethyl-3-[(3E,7E,11E,15E)-3,7,12,16,20-pentamethylhenicosa-3,7,11,15,19-pentaen-1-yl]oxirane
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30C
0.0338 - 0.0511
(S)-2,3-oxidosqualene
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0000128 - 0.77
(S)-2,3-oxidosqualene
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0000025 - 22.83
(S)-2,3-oxidosqualene
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00000698
(4-bromophenyl)[2-fluoro-4-([6-[methyl(prop-2-en-1-yl)amino]hexyl]oxy)phenyl]methanone
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pH 7, 30C
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0.0000134
Iminosqualene
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pH 7, 30C
0.000102
N,N-diethyl-2-[[(3beta)-17-methylideneandrost-5-en-3-yl]oxy]ethanamine
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pH 7, 30C
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0000107
(4-bromophenyl)[2-fluoro-4-([6-[methyl(prop-2-en-1-yl)amino]hexyl]oxy)phenyl]methanone
Euphorbia tirucalli
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pH 7, 30C
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0.1
10-aza-10,11-dihydro-2,3-oxidosqualene
Pisum sativum
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0.015
19-aza-18,19,22,23-tetrahydro-2,3-oxidosqualene
Pisum sativum
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0.04
23-aza-22,23-dihydro-2,3-oxidosqualene
Pisum sativum
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30C
0.0000309
Iminosqualene
Euphorbia tirucalli
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pH 7, 30C
0.000142
N,N-diethyl-2-[[(3beta)-17-methylideneandrost-5-en-3-yl]oxy]ethanamine
Euphorbia tirucalli
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pH 7, 30C
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.352
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pH 7, 30C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
in five-day old dark-grown seedling, enzyme expression is strongly induced by light, weakly induced by methyl jasmonate and low temperature, and not induced by elicitor or UV-B treatment
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
additional information
OXA1 is deficient in roots of early reproductive stage
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
77000
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SDS-PAGE
87000
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calculated from cDNA
87350
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calculated from cDNA
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
thin-layer chromatography
using Ni-NTA chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed as a polyhistidine-tagged protein in Saccharomyces cerevisiae GIL77, which lacks the lanosterol synthase gene. Expression yield: 5-7 mg
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expressed in a lanosterol synthase deficient Saccharomyces cerevisiae strain
expressed in Medicago truncatula
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expressed in Nicotiana benthamiana leaves and in Pichia methanolica
expressed in Saccharomyces cerevisiae mutant GIL77; expressed in Saccharomyces cerevisiae mutant strain GIL77
expressed in Saccharomyces cerevisiae strain YNN295
expressed in yeast
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expression in Pichia pastoris
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expression in Saccharomyces cerevisae
expression in Saccharomyces cerevisiae
expression of PtBS in the triterpenoid synthase-deficient yeast mutant GIL77 leads to the production of beta-amyrin as sole product
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functional expression of ObAS1 in Saccharomyces cerevisiae leads to the production of beta-amyrin
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
after 24 h of elicitation, beta-amyrin synthase transcripts are increased at 0.1, 1, and 2 mM of methyl jasmonate, and they are increased at 0.1 and 1 mM salicylic acid
CrAS is preferentially expressed in leaf epidermis, in younger leaves and during the earlier stages of seedling development in Catharanthus roseus
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highest expression in roots
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the treatment with 0.1 mM methyl jasmonate yields greater accumulation of beta-amyrin as well as B-AS activity
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
C486A
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mutant shows 46% activity compared to wild-type (100%), Km similar to wild-type, kcat decreased
C564A
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mutant shows 1.6% activity compared to wild-type (100%), Km increased compared to wild-type, kcat highly decreased
D485E
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mutant shows no activity
D485N
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mutant shows no activity
F728A
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highly reduced activity compared to wild-type
F728H
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highly reduced activity compared to wild-type
F728I
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highly reduced activity compared to wild-type
F728M
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highly reduced activity compared to wild-type
F728W
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highly reduced activity compared to wild-type
F728Y
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activity comparable to wild-type
C262S
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mutation in region responsible for product differentiation. Like wild-type, mutant produces beta-amyrin as sole product
M258I/W259L
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mutation in region responsible for product differentiation. Mutant produces 40.5% beta-amyrin, 53.4% lupeol, 3.6% butyrospermol and 2.5% germanicol
W259L
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mutation in region responsible for product differentiation. Mutant produces 30.3% beta-amyrin, 54.6% lupeol, 3.6% butyrospermol and 3.4% germanicol
Y261H
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mutation in region responsible for product differentiation. Mutant produces 2.4% lupeol, 13.6% germanicol and 84% of dammara-18(E),21-dien-3beta-ol, dammara-18(Z),21-dien-3beta-ol and dammara-18(28),21-dien-3beta-ol
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis