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
5.4.99.39
-
RECOMMENDED NAME
GeneOntology No.
beta-amyrin synthase
-
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(3S)-2,3-epoxy-2,3-dihydrosqualene = beta-amyrin
show the reaction diagram
-
-
-
-
(3S)-2,3-epoxy-2,3-dihydrosqualene = beta-amyrin
show the reaction diagram
no scrambling of methyl groups is observed during beta-amyrin formation, the isopropyl group of the lupenyl cation intermediate must be held tightly during product formation
-
(3S)-2,3-epoxy-2,3-dihydrosqualene = beta-amyrin
show the reaction diagram
substrate is used in chair-chair-chair-boat conformation. Cyclization first generates the tetracyclic dammarenyl C20 cation with the 17beta-side chain
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
avenacin biosynthesis, initial reactions
-
-
Biosynthesis of secondary metabolites
-
-
ginsenosides biosynthesis
-
-
mangrove triterpenoid biosynthesis
-
-
oleanolate biosynthesis
-
-
pentacyclic triterpene biosynthesis
-
-
Sesquiterpenoid and triterpenoid biosynthesis
-
-
soybean saponin I biosynthesis
-
-
superpathway avenacin A biosynthesis
-
-
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
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
var. japonica
Uniprot
Manually annotated by BRENDA team
cultivar Jack
-
-
Manually annotated by BRENDA team
induction by wounding
SwissProt
Manually annotated by BRENDA team
high expression of enzyme from day 4 to day 20 in medium inducing soyasaponin production, low level of expression after day 24 or in standard medium
-
-
Manually annotated by BRENDA team
; recombinant protein
-
-
Manually annotated by BRENDA team
recombinant enzyme
-
-
Manually annotated by BRENDA team
recombinant protein
-
-
Manually annotated by BRENDA team
cultivars MicroTom, M82, and Ailsa Craig
-
-
Manually annotated by BRENDA team
variants M82, Ailsa Craig, and MicroTom
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
-
saponin biosynthesis in soybean seeds is suppressed through RNA interference-mediated beta-amyrin synthase gene silencing
metabolism
-
expression of PtBS in the triterpenoid synthase-deficient yeast mutant GIL77 leads to the production of beta-amyrin as sole product
metabolism
-
functional expression of ObAS1 in Saccharomyces cerevisiae leads to the production of beta-amyrin
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
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
-
pre-chair-chair-chair-boat conformation of substrate
about 1% of the yield with substrate 24,30-bisnor-2,3-oxidosqualene
-
?
(3S)-2,3-epoxy-2,3-dihydrosqualene
beta-amyrin
show the reaction diagram
E7DN63
-
isoform SITT1 produces 13% beta-amyrin
-
?
(3S)-2,3-oxidosqualene
beta-amyrin
show the reaction diagram
-
-
-
-
?
(S)-2,3-oxidosqualene
beta-amyrin
show the reaction diagram
-
-
-
-
?
(S)-2,3-oxidosqualene
beta-amyrin
show the reaction diagram
-
-
-
-
?
(S)-2,3-oxidosqualene
beta-amyrin
show the reaction diagram
-
-
-
-
?
(S)-2,3-oxidosqualene
beta-amyrin
show the reaction diagram
-
-
-
-
?
(S)-2,3-oxidosqualene
beta-amyrin
show the reaction diagram
Q401R6
-
-
-
?
(S)-2,3-oxidosqualene
beta-amyrin
show the reaction diagram
-
-
-
-
?
(S)-2,3-oxidosqualene
beta-amyrin
show the reaction diagram
Q84PE3
-
-
-
?
(S)-2,3-oxidosqualene
beta-amyrin
show the reaction diagram
-
-
-
-
?
(S)-2,3-oxidosqualene
beta-amyrin
show the reaction diagram
B6EXY6
-
-
-
?
(S)-2,3-oxidosqualene
beta-amyrin
show the reaction diagram
Q5D7Q8
-
-
-
?
(S)-2,3-oxidosqualene
beta-amyrin
show the reaction diagram
-
-
-
-
?
(S)-2,3-oxidosqualene
beta-amyrin
show the reaction diagram
Q9MB42
-
-
-
?
(S)-2,3-oxidosqualene
beta-amyrin
show the reaction diagram
E7DN63
-
-
-
?
(S)-2,3-oxidosqualene
beta-amyrin
show the reaction diagram
-
-
-
-
?
2,3-oxidosqualene
beta-amyrin
show the reaction diagram
-
-
-
-
?
2,3-oxidosqualene
beta-amyrin
show the reaction diagram
-
-
-
-
?
2,3-oxidosqualene
beta-amyrin
show the reaction diagram
-
-
-
-
?
2,3-oxidosqualene
beta-amyrin
show the reaction diagram
Q8W3Z1
-
-
-
?
2,3-oxidosqualene
beta-amyrin
show the reaction diagram
O82140
-
-
-
?
2,3-oxidosqualene
beta-amyrin
show the reaction diagram
-
-
sole product
-
?
2,3-oxidosqualene
beta-amyrin
show the reaction diagram
A8CDT2
-
sole product
-
?
2,3-oxidosqualene
beta-amyrin
show the reaction diagram
-
-
sole product
-
?
22,23-dihydro-2,3-oxidosqualene
euph-7-en-3beta-ol + bacchar-12-en-3beta-ol
show the reaction diagram
-
-
about 10% of the yield with substrate 24,30-bisnor-2,3-oxidosqualene
-
?
22,23-dihydro-2,3-oxidosqualene
euph-7-en-3beta-ol + bacchar-12-en-3beta-ol
show the reaction diagram
-
substrate is in a chair-chair-chair-boat conformation
4:1 mixture of euph-7-en-3beta-ol and bacchar-12-en-3beta-ol
-
?
24,30-bisnor-2,3-oxidosqualene
29,30-bisnor-beta-amyrin + 29,30-bisnorgermanicol + 29,30-bisnor-delta-amyrin
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
-
-
3:1:0.2 mixture of 29,30-bisnor-beta-amyrin, 29,30-bisnorgermanicol and 29,30-bisnor-delta-amyrin, 3:1:0.2 product ratio
-
?
additional information
?
-
-
enzyme is involved in saponin biosynthesis
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(S)-2,3-oxidosqualene
beta-amyrin
show the reaction diagram
-
-
-
-
?
additional information
?
-
-
enzyme is involved in saponin biosynthesis
-
-
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(4-bromophenyl)[2-fluoro-4-([6-[methyl(prop-2-en-1-yl)amino]hexyl]oxy)phenyl]methanone
-
-
-
10-aza-10,11-dihydro-2,3-oxidosqualene
-
-
19-aza-18,19,22,23-tetrahydro-2,3-oxidosqualene
-
-
23-aza-22,23-dihydro-2,3-oxidosqualene
-
-
Iminosqualene
-
-
N,N-diethyl-2-[[(3beta)-17-methylideneandrost-5-en-3-yl]oxy]ethanamine
-
-
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Triton X-100
-
at 0.05% highest activity of the enzyme
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
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
-
30C
0.0338
(S)-2,3-oxidosqualene
-
pH 7, 30C, wild-type
0.0348
(S)-2,3-oxidosqualene
-
pH 7, 30C, mutant C486A
0.0511
(S)-2,3-oxidosqualene
-
pH 7, 30C, mutant C564A
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0000128
(S)-2,3-oxidosqualene
-
pH 7, 30C, mutant C564A
0.34
(S)-2,3-oxidosqualene
-
pH 7, 30C, mutant C486A
0.77
(S)-2,3-oxidosqualene
-
pH 7, 30C, wild-type
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0000025
(S)-2,3-oxidosqualene
-
pH 7, 30C, mutant C564A
6882
9.8
(S)-2,3-oxidosqualene
-
pH 7, 30C, mutant C486A
6882
22.83
(S)-2,3-oxidosqualene
-
pH 7, 30C, wild-type
6882
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00000698
(4-bromophenyl)[2-fluoro-4-([6-[methyl(prop-2-en-1-yl)amino]hexyl]oxy)phenyl]methanone
-
pH 7, 30C
-
0.0000134
Iminosqualene
-
pH 7, 30C
0.000102
N,N-diethyl-2-[[(3beta)-17-methylideneandrost-5-en-3-yl]oxy]ethanamine
-
pH 7, 30C
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0000107
(4-bromophenyl)[2-fluoro-4-([6-[methyl(prop-2-en-1-yl)amino]hexyl]oxy)phenyl]methanone
-
pH 7, 30C
-
0.1
10-aza-10,11-dihydro-2,3-oxidosqualene
-
-
0.015
19-aza-18,19,22,23-tetrahydro-2,3-oxidosqualene
-
-
0.04
23-aza-22,23-dihydro-2,3-oxidosqualene
-
30C
0.0000309
Iminosqualene
-
pH 7, 30C
0.000142
N,N-diethyl-2-[[(3beta)-17-methylideneandrost-5-en-3-yl]oxy]ethanamine
-
pH 7, 30C
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.352
-
pH 7, 30C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
moderate expression
Manually annotated by BRENDA team
-
predominant expression in leaf
Manually annotated by BRENDA team
-
minor expression
Manually annotated by BRENDA team
Q5D7Q8
the transcript level of OXA1 is very low in leaf during early vegetative stages as compared to early reproductive stages
Manually annotated by BRENDA team
-
of root and leaf of stem
Manually annotated by BRENDA team
-
highest expression
Manually annotated by BRENDA team
O82140
hairy root
Manually annotated by BRENDA team
-
adventitious roots
Manually annotated by BRENDA team
-
moderate expression
Manually annotated by BRENDA team
-
immature seed
Manually annotated by BRENDA team
Q8H2B0
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
-
moderate expression
Manually annotated by BRENDA team
-
leaf epidermis is the preferred site of CrAS expression. CrAS is preferentialy expressed in younger leaves
Manually annotated by BRENDA team
additional information
Q5D7Q8
OXA1 is deficient in roots of early reproductive stage
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
77000
-
SDS-PAGE
729707
87000
-
calculated from cDNA
730640
87350
-
calculated from cDNA
730595
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
Q8H2B0
x * 84000, calculated
?
-
x * 87500, calculated
?
-
x * 87500, calculated
?
O82140
x * 88000, calculated
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
using Ni-NTA chromatography
-
thin-layer chromatography
E7DN63
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in a lanosterol synthase deficient Saccharomyces cerevisiae strain
B6EXY6
expression in Saccharomyces cerevisiae
-
expressed in Medicago truncatula
-
expressed in Saccharomyces cerevisiae strain YNN295
Q5D7Q8
expression in Saccharomyces cerevisae
Q8W3Z1
expression in Saccharomyces cerevisiae
A8CDT2
expressed in yeast
-
expressed as a polyhistidine-tagged protein in Saccharomyces cerevisiae GIL77, which lacks the lanosterol synthase gene. Expression yield: 5-7 mg
-
expression in Pichia pastoris
-
expression in Saccharomyces cerevisiae
-
expression in Saccharomyces cerevisiae
-
expressed in Nicotiana benthamiana leaves and in Pichia methanolica
C7SCX1
expression in Saccharomyces cerevisiae
Q84PE3
functional expression of ObAS1 in Saccharomyces cerevisiae leads to the production of beta-amyrin
-
expression in Saccharomyces cerevisae
O82140
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
-
expressed in Saccharomyces cerevisiae mutant GIL77; expressed in Saccharomyces cerevisiae mutant strain GIL77
E7DN63
expression in Saccharomyces cerevisiae
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
CrAS is preferentially expressed in leaf epidermis, in younger leaves and during the earlier stages of seedling development in Catharanthus roseus
-
the treatment with 0.1 mM methyl jasmonate yields greater accumulation of beta-amyrin as well as B-AS activity
-
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
Q9MB42
the treatment with 0.1 mM methyl jasmonate yields greater accumulation of beta-amyrin as well as B-AS activity
-
highest expression in roots
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
C486A
-
mutant shows 46% activity compared to wild-type (100%), Km similar to wild-type, kcat decreased
C564A
-
mutant shows 1.6% activity compared to wild-type (100%), Km increased compared to wild-type, kcat highly decreased
D485E
-
mutant shows no activity
D485N
-
mutant shows no activity
F728A
-
highly reduced activity compared to wild-type
F728H
-
highly reduced activity compared to wild-type
F728I
-
highly reduced activity compared to wild-type
F728M
-
highly reduced activity compared to wild-type
F728W
-
highly reduced activity compared to wild-type
C262S
-
mutation in region responsible for product differentiation. Like wild-type, mutant produces beta-amyrin as sole product
W259L
-
mutation in region responsible for product differentiation. Mutant produces 30.3% beta-amyrin, 54.6% lupeol, 3.6% butyrospermol and 3.4% germanicol
additional information
-
construction of chimeric proteins using beta-amyrin synthase from Panax ginseng and lupeol synthase from Arabidopsis thaliana. Chimera with N-terminal half of beta-amyrin synthase and C-terminal half of lupeol synthase produces beta-amyrin and lupeol in ratio 3:1. Chimera with only the second quarter of the N-terminus from beta-amyrin synthase, produces beta-amyrin and lupeol in a 4:1 ratio, while another chimera created by mixed PCR produces beta-amyrin and lupeol in a 1:4 ratio
additional information
-
functional expression in Saccharomyces cerevisiae results in production of beta-amyrin
additional information
Q8W3Z1
functional expression in Saccharomyces cerevisiae mutant lacking lanosterol synthase activity results in production of beta-amyrin
additional information
A8CDT2
functional expression in Saccharomyces cerevisiae results in production of beta-amyrin
F728Y
-
activity comparable to wild-type
additional information
-
functional expression in Pichia pastoris results in production of beta-amyrin
additional information
-
functional expression in Saccharomyces cerevisiae mutant lacking lanosterol synthase activity results in production of beta-amyrin
additional information
-
functional expression in Saccharomyces cerevisiae mutant with disruption in oxidosqualene cyclase gene results in production of beta-amyrin
additional information
Q84PE3
functional expression in Saccharomyces cerevisiae results in production of beta-amyrin
M258I/W259L
-
mutation in region responsible for product differentiation. Mutant produces 40.5% beta-amyrin, 53.4% lupeol, 3.6% butyrospermol and 2.5% germanicol
additional information
O82140
functional expression in Saccharomyces cerevisiae mutant lacking lanosterol synthase activity results in production of beta-amyrin
Y261H
-
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
-
functional expression in Saccharomyces cerevisiae mutant lacking lanosterol synthase activity results in production of beta-amyrin
additional information
-
functional expression in Saccharomyces cerevisiae results in production of beta-amyrin
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
-
engineering of the sterol pathway in Saccharomyces cerevisiae for production of beta-amyrin. Expression of enzyme gene plus manipulation of 3-hydroxy-3-methylglutaryl-CoA reductase and lanosterol synthase in Saccharomyces cerevisiae leads to levels of 6 mg beta-amyrin per l of culture
synthesis
-
use of enzyme for production of unnatural tetracyclic sesterterpenes