Information on EC 4.3.3.2 - strictosidine synthase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
4.3.3.2
-
RECOMMENDED NAME
GeneOntology No.
strictosidine synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
3-alpha(S)-strictosidine + H2O = tryptamine + secologanin
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
condensation
condensation of aldehyde function with amine function
-
-
-
-
Pictete-Spengler reaction
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
-
camptothecin biosynthesis
-
-
Indole alkaloid biosynthesis
-
-
Metabolic pathways
-
-
secologanin and strictosidine biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
3-alpha(S)-strictosidine tryptamine-lyase (secologanin-forming)
Catalyses a Pictet-Spengler reaction between the aldehyde group of secologanin and the amino group of tryptamine [4,5]. Involved in the biosynthesis of the monoterpenoid indole alkaloids.
CAS REGISTRY NUMBER
COMMENTARY hide
69669-72-3
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Amsonia salicifolia
-
-
-
Manually annotated by BRENDA team
Catharanthus pusillus
-
-
-
Manually annotated by BRENDA team
transformed with Agrobacterium tumefaciens to enable growth in the absence of exogenous plant growth regulators
-
-
Manually annotated by BRENDA team
Cinchona robusta
-
-
-
Manually annotated by BRENDA team
Ervatamia divaricatum
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Stemmadenia tomentosa var. palmeri
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
-
strictosidine synthases belong to the beta-propeller fold family characterized by an all-beta architecture with four to eight blades, each consisting of four antiparallel beta-sheets, arranged around a pseudo symmetry axis
metabolism
-
the enzyme is involved in biosynthesis of 3-alpha(S)-strictosidine, a glycosylated indole alkaloid and central precursor of the entire monoterpenoid indole alkaloid biosynthesis, from tryptamine and secologanin and of dolichantoside from N-omega-methyltryptamine and secologanin
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2R)-tryptophanol + H2O
?
show the reaction diagram
-
substrate for discovery of active mutants
-
-
?
(2S)-tryptophanol + H2O
?
show the reaction diagram
-
substrate for discovery of active mutants
-
-
?
2-(1-benzothien-3-yl)ethanamine + secologanin
(4S,5R,6S)-4-[(S)-1-(1,2,3,4-tetrahydro-benzo[4,5]thieno[2,3-c]pyridin-1-yl)methyl]-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5-vinyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester + H2O
show the reaction diagram
-
-
-
-
?
2-(4-fluoro-1H-indol-3-yl)ethanamine + secologanin
(4S,5R,6S)-4-((S)-5-fluoro-2,3,4,9-tetrahydro-1H-b-carbolin-1-ylmethyl)-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5-vinyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester + H2O
show the reaction diagram
-
-
-
-
?
2-(4-methyl-1H-indol-3-yl)ethanamine + secologanin
(4S,5R,6S)-4-((S)-5-methyl-2,3,4,9-tetrahydro-1H-b-carbolin-1-ylmethyl)-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5-vinyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester + H2O
show the reaction diagram
-
-
-
-
?
2-(5-fluoro-1H-indol-3-yl)ethanamine + secologanin
(4S,5R,6S)-4-((S)-6-fluoro-2,3,4,9-tetrahydro-1H-b-carbolin-1-ylmethyl)-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5-vinyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester + H2O
show the reaction diagram
-
-
-
-
?
2-(6-fluoro-1H-indol-3-yl)ethanamine + secologanin
(4S,5R,6S)-4-((S)-7-fluoro-2,3,4,9-tetrahydro-1H-b-carbolin-1-ylmethyl)-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5-vinyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester + H2O
show the reaction diagram
-
-
-
-
?
2-(7-fluoro-1H-indol-3-yl)ethanamine + secologanin
(4S,5R,6S)-4-((S)-8-fluoro-2,3,4,9-tetrahydro-1H-b-carbolin-1-ylmethyl)-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5-vinyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester + H2O
show the reaction diagram
-
-
-
-
?
2-(7-methyl-1H-indol-3-yl)ethanamine + secologanin
(4S,5R,6S)-4-((S)-8-methyl-2,3,4,9-tetrahydro-1H-b-carbolin-1-ylmethyl)-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5-vinyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester + H2O
show the reaction diagram
-
-
-
-
?
2-benzofuran-3-yl-ethylamine + secologanin
(4S,5R,6S)-4-[(S)-1-(1,2,3,4-tetrahydro-benzo[4,5]furo[2,3-c]pyridin-1-yl)methyl]-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5-vinyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester + H2O
show the reaction diagram
-
-
-
-
?
3-(2-aminoethyl)-1H-indol-5-ol + secologanin
(4S,5R,6S)-4-((S)-6-hydroxy-2,3,4,9-tetrahydro-1H-b-carbolin-1-ylmethyl)-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5-vinyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester + H2O
show the reaction diagram
-
-
-
-
?
3-(2-aminoethyl)-benzothiophene + secologanin
? + H2O
show the reaction diagram
-
-
-
?
3-alpha(S)-strictosidine + H2O
tryptamine + secologanin
show the reaction diagram
3-[(tert-butoxycarbonyl)amino]propyl (2S,3R,4S)-3-ethenyl-2-(beta-D-glucopyranosyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate + secologanin
? + H2O
show the reaction diagram
-
competitive to strictosidine
-
-
?
4-fluorotryptamine + secologanin
4-fluoro-3-alpha(S)-strictosidine + H2O
show the reaction diagram
-
-
-
?
4-methyltryptamine + secologanin
4-methyl-3-alpha(S)-strictosidine + H2O
show the reaction diagram
-
-
-
?
4-methyltryptamine + secologanin
? + H2O
show the reaction diagram
poor substrate
-
-
?
5,6-dihydroxytryptamine
?
show the reaction diagram
-
-
-
?
5,6-dihydroxytryptamine + secologanin
? + H2O
show the reaction diagram
-
-
-
-
?
5-bromotryptamine + H2O
?
show the reaction diagram
-
substrate for discovery of active mutants
-
-
?
5-chlorotryptamine + H2O
?
show the reaction diagram
-
substrate for discovery of active mutants
-
-
?
5-fluoro-tryptamine + H2O
?
show the reaction diagram
-
-
-
-
?
5-fluorotryptamine
?
show the reaction diagram
-
-
-
?
5-fluorotryptamine + secologanin
5-fluoro-3-alpha(S)-strictosidine + H2O
show the reaction diagram
5-fluorotryptamine + secologanin
?
show the reaction diagram
-
6% of the activity with trypamine
-
-
?
5-hydroxy-tryptamine + H2O
?
show the reaction diagram
-
-
-
-
?
5-hydroxytryptamine + secologanin
?
show the reaction diagram
-
4% of the activity with trypamine
-
-
?
5-hydroxytryptamine + secologanin
? + H2O
show the reaction diagram
poor substrate
-
-
?
5-methoxy-tryptamine + H2O
?
show the reaction diagram
-
-
-
-
?
5-methoxytryptamine + secologanin
10-methoxystrictosidine
show the reaction diagram
Cinchona robusta
-
10% of activity
-
?
5-methoxytryptamine + secologanin
? + H2O
show the reaction diagram
poor substrate
-
-
?
5-methyl-tryptamine + H2O
?
show the reaction diagram
-
-
-
-
?
5-methyltryptamine + H2O
?
show the reaction diagram
-
substrate for discovery of active mutants
-
-
?
6-fluoro-tryptamine + H2O
?
show the reaction diagram
-
-
-
-
?
6-fluorotryptamine
?
show the reaction diagram
-
-
-
?
6-fluorotryptamine + secologanin
6-fluoro-3-alpha(S)-strictosidine + H2O
show the reaction diagram
6-hydroxytryptamine + secologanin
?
show the reaction diagram
-
9% of the activity with trypamine
-
-
?
6-methoxy-tryptamine + H2O
?
show the reaction diagram
-
-
-
-
?
6-methoxyltryptamine + secologanin
6-methoxy-3-alpha(S)-strictosidine + H2O
show the reaction diagram
-
-
-
-
?
6-methoxytryptamine
?
show the reaction diagram
-
-
-
?
6-methoxytryptamine + secologanin
? + H2O
show the reaction diagram
poor substrate
-
-
?
6-methyl-tryptamine + H2O
?
show the reaction diagram
-
-
-
-
?
6-methyltryptamine + secologanin
6-methyl-3-alpha(S)-strictosidine + H2O
show the reaction diagram
7-azatryptamine + secologanin
3-alpha(S)-12-azastrictosidine
show the reaction diagram
-
assay at pH 7.0, 28C, reaction stopped by adding methanol
-
-
?
7-fluorotryptamine + secologanin
7-fluoro-3-alpha(S)-strictosidine + H2O
show the reaction diagram
-
-
-
?
7-fluorotryptamine + secologanin
?
show the reaction diagram
-
8% of the activity with trypamine
-
-
?
7-methyltryptamine
?
show the reaction diagram
-
-
-
?
7-methyltryptamine + secologanin
7-methyl-3-alpha(S)-strictosidine + H2O
show the reaction diagram
7-methyltryptamine + secologanin
?
show the reaction diagram
-
15% of the activity with trypamine
-
-
?
7-methyltryptamine + secologanin
? + H2O
show the reaction diagram
poor substrate
-
-
?
but-3-yn-1-yl (2S,3R,4S)-3-ethenyl-2-(beta-D-glucopyranosyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate + secologanin
? + H2O
show the reaction diagram
-
competitive to strictosidine
-
-
?
D-tryptophan + H2O
?
show the reaction diagram
-
substrate for discovery of active mutants
-
-
?
D-tryptophan methyl ester + H2O
?
show the reaction diagram
-
substrate for discovery of active mutants
-
-
?
L-tryptophan + H2O
?
show the reaction diagram
-
substrate for discovery of active mutants
-
-
?
methyl (2R,4S)-2-(2-methylpropoxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate + tryptamine
methyl (2R,4S)-2-(2-methylpropoxy)-4-[(1S)-2,3,4,9-tetrahydro-1H-beta-carbolin-1-ylmethyl]-3,4-dihydro-2H-pyran-5-carboxylate + H2O
show the reaction diagram
-
cis- and trans-isomers are equally well accepted as substrates
-
-
?
methyl (2R,4S)-2-(cyclohexyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate + tryptamine
methyl (2R,4S)-2-(cyclohexyloxy)-4-[(1S)-2,3,4,9-tetrahydro-1H-beta-carbolin-1-ylmethyl]-3,4-dihydro-2H-pyran-5-carboxylate + H2O
show the reaction diagram
-
significant preference for the trans-isomer
-
-
?
methyl (2R,4S)-2-ethoxy-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate + tryptamine
methyl (2R,4S)-2-ethoxy-4-[(1S)-2,3,4,9-tetrahydro-1H-beta-carbolin-1-ylmethyl]-3,4-dihydro-2H-pyran-5-carboxylate + H2O
show the reaction diagram
-
cis- and trans-isomers are equally well accepted as substrates
-
-
?
methyl (2R,4S)-2-tert-butoxy-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate + tryptamine
methyl (2R,4S)-2-tert-butoxy-4-[(1S)-2,3,4,9-tetrahydro-1H-beta-carbolin-1-ylmethyl]-3,4-dihydro-2H-pyran-5-carboxylate + H2O
show the reaction diagram
-
cis- and trans-isomers are equally well accepted as substrates
-
-
?
methyl (2S,4S)-2-(2-methylpropoxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate + tryptamine
methyl (2S,4S)-2-(2-methylpropoxy)-4-[(1S)-2,3,4,9-tetrahydro-1H-beta-carbolin-1-ylmethyl]-3,4-dihydro-2H-pyran-5-carboxylate + H2O
show the reaction diagram
-
cis- and trans-isomers are equally well accepted as substrates
-
-
?
methyl (2S,4S)-2-ethoxy-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate + tryptamine
methyl (2S,4S)-2-ethoxy-4-[(1S)-2,3,4,9-tetrahydro-1H-beta-carbolin-1-ylmethyl]-3,4-dihydro-2H-pyran-5-carboxylate + H2O
show the reaction diagram
-
cis- and trans-isomers are equally well accepted as substrates
-
-
?
methyl (2S,4S)-2-tert-butoxy-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate + tryptamine
methyl (2S,4S)-2-tert-butoxy-4-[(1S)-2,3,4,9-tetrahydro-1H-beta-carbolin-1-ylmethyl]-3,4-dihydro-2H-pyran-5-carboxylate + H2O
show the reaction diagram
-
cis- and trans-isomers are equally well accepted as substrates
-
-
?
N-omega-methyltryptamine + secologanin
dolichantoside + H2O
show the reaction diagram
-
-
-
-
?
prop-2-yn-1-yl (2S,3R,4S)-3-ethenyl-2-(beta-D-glucopyranosyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate + secologanin
? + H2O
show the reaction diagram
-
competitive to strictosidine
-
-
?
secologanin + tryptamine
3-alpha(S)-strictosidine + H2O
show the reaction diagram
-
-
-
-
?
serotonin
?
show the reaction diagram
-
-
-
?
serotonin + secologanin
5-hydroxy-3-alpha(S)-strictosidine + H2O
show the reaction diagram
tryptamine + 2'-O-methylsecologanin
?
show the reaction diagram
-
-
-
-
?
tryptamine + 2'-O-methylsecologanin
? + H2O
show the reaction diagram
-
-
-
-
?
tryptamine + 3'-O-methylsecologanin
?
show the reaction diagram
-
-
-
-
?
tryptamine + 3'-O-methylsecologanin
? + H2O
show the reaction diagram
-
-
-
-
?
tryptamine + dihydrosecologanin
?
show the reaction diagram
-
-
-
-
?
tryptamine + secologanic acid allyl ester
? + H2O
show the reaction diagram
-
-
-
-
?
tryptamine + secologanic acid pentynyl ester
? + H2O
show the reaction diagram
-
-
-
-
?
tryptamine + secologanic acid propynyl ester
? + H2O
show the reaction diagram
-
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
show the reaction diagram
tryptamine + secologanin
3alpha(S)-strictosidine
show the reaction diagram
tryptamine + secologanin
? + H2O
show the reaction diagram
poor substrate
-
-
?
additional information
?
-
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
3-alpha(S)-strictosidine + H2O
tryptamine + secologanin
show the reaction diagram
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
show the reaction diagram
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3-alpha(S)-strictosidine
Cinchona robusta
-
-
3-[(tert-butoxycarbonyl)amino]propyl (3R,4S)-3-ethenyl-2-(beta-D-glucopyranosyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate
-
-
4-(2-aminoethyl)-benzenesulfonyl fluoride
-
4 mM, 4% inactivation after 30 min and 12% inactivation after 120 min in 100 mM potassium phosphate buffer, pH 7.0
chinconine
Cinchona robusta
-
-
-
cinchonidine
Cinchona robusta
-
-
corynantheal
Cinchona robusta
-
-
Cu2+
Cinchona robusta
-
-
Diethylpyrocarbonate
-
1 mM, 49% inactivation after 30 min and 63% inactivation after 120 min in 100 mM potassium phosphate, pH 6.0
Dihydroquinine
Cinchona robusta
-
-
Dinitrofluorobenzene
-
5 mM, no inactivation after 30 min and 15% inactivation after 120 min in Tris-HCl, pH 8.0
-
N,N'-dicyclohexylcarbodiimide
-
0.05 mM, complete inactivation after 30 min in MES, pH 6.0
N-Acetylimidazole
-
10 mM, 5% inactivation after 30 min and 12% inactivation after 120 min in Tris-HCl, pH 8.0
N-ethyl-5-phenylisoxazolium-3'-sulfonate
-
1 mM leads to 48% inactivation after 30 min and 53% inactivation after 120 min in MES, pH 6.0, 5 mM leads to 80% inactivation after 30 min and 100% inactivation after 120 min in MES, pH 6.0
p-chlormercuribenzoate
-
1 mM, 34% inactivation after 30 min and 35% inactivation after 120 min in 100 mM potassium phosphate, pH 6.0
p-chloromercuribenzoate
quinidine
Cinchona robusta
-
-
Quinine
Cinchona robusta
-
-
Tris
Cinchona robusta
-
-
tryptamine
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
bovine serum albumin
-
1 mg/ml stimulates activity
-
additional information
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.94
(2'R)-tryptophanol
-
mutant F232L
0.042
2-(4-fluoro-1H-indol-3-yl)ethanamine
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
0.08
2-(4-methyl-1H-indol-3-yl)ethanamine
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
0.0071
2-(5-fluoro-1H-indol-3-yl)ethanamine
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
0.0089
2-(6-fluoro-1H-indol-3-yl)ethanamine
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
0.013
2-(7-fluoro-1H-indol-3-yl)ethanamine
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
0.198
2-(7-methyl-1H-indol-3-yl)ethanamine
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
0.0077
2-benzofuran-3-yl-ethylamine
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
8
3'-O-methylsecologanin
-
pH 7.0, 35C
1.2
3-(2-aminoethyl)-1H-indol-5-ol
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
0.259 - 1.302
5-fluoro-tryptamine
0.844 - 2.255
5-hydroxy-tryptamine
3.592
5-methoxy-tryptamine
-
mutant V208A
0.281
5-methyl-tryptamine
-
mutant V208A
0.37
5-methyltryptamine
-
mutant V214M
0.136 - 0.356
6-fluoro-tryptamine
0.307 - 0.962
6-methoxy-tryptamine
0.393 - 0.762
6-methyl-tryptamine
3.5
dihydrosecologanin
-
pH 7.0, 35C
0.039 - 5.07
secologanin
1.036
serotonin
-
wild-type enzyme
0.0014 - 5.8
tryptamine
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.058
2-(4-fluoro-1H-indol-3-yl)ethanamine
Escherichia coli
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
0.0031
2-(4-methyl-1H-indol-3-yl)ethanamine
Escherichia coli
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
0.0072
2-(5-fluoro-1H-indol-3-yl)ethanamine
Escherichia coli
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
0.0093
2-(6-fluoro-1H-indol-3-yl)ethanamine
Escherichia coli
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
0.0018
2-(7-fluoro-1H-indol-3-yl)ethanamine
Escherichia coli
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
0.0048
2-(7-methyl-1H-indol-3-yl)ethanamine
Escherichia coli
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
0.0038
2-benzofuran-3-yl-ethylamine
Escherichia coli
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
0.0016
3-(2-aminoethyl)-1H-indol-5-ol
Escherichia coli
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
3.4 - 37.46
5-fluoro-tryptamine
0.025 - 562.1
5-hydroxy-tryptamine
0.21 - 79.66
5-methoxy-tryptamine
0.03 - 6.56
5-methyl-tryptamine
0.52 - 23.37
6-fluoro-tryptamine
0.97 - 16.66
6-methoxy-tryptamine
0.057 - 10.95
6-methyl-tryptamine
4.5
secologanin
Rauvolfia serpentina
-
in reaction with tryptamine
11.13
serotonin
Rauvolfia serpentina
-
wild-type enzyme
0.002 - 54.09
tryptamine
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.007
Quinine
Cinchona robusta
-
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.000003
3-[(tert-butoxycarbonyl)amino]propyl (3R,4S)-3-ethenyl-2-(beta-D-glucopyranosyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate
Catharanthus roseus
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.35
-
purified enzyme, pH 7.5, 30C
1.07
-
purified enzyme, pH 7.0, 35C
2.18
-
purified enzyme, pH 6.5
3.72
-
purified enzyme
11.04
-
purified enzyme
31.62
-
purified enzyme, pH 6.8, 30C
additional information
-
activities between 14.29 nKat/l and 67.15 nKat/l, depending on expression system, increased activity in presence of chaperone pG-Tf2
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 8.5
Cinchona robusta
-
-
6.4
-
immobilized enzyme
6.5 - 7
Amsonia salicifolia
-
slightly higher activity in phosphate than in Tris/HCl buffer
6.9
Catharanthus pusillus
-
-
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
3 - 9
-
immobilized enzyme
4 - 8.5
-
soluble enzyme
5 - 7.5
-
50% activity
5 - 8
-
50% activity
5.5 - 9.5
Cinchona robusta
-
50% activity
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
35
-
assay at
45 - 50
Amsonia salicifolia
-
-
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.19
sequence calculation
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
of aerial organs. Coexpression of strictosidine synthase and strictosidine beta-D-glucosidase in the epidermal first barrier
Manually annotated by BRENDA team
hairy root and root, high expression
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30000
-
gel filtration
31000
-
isoform III, gel filtration
33000
Cinchona robusta
-
SDS-PAGE, isoform I b and II b
34000
-
gel filtration
35300
-
calculated, SDS-PAGE
37000
-
determined by SDS-PAGE
38000
-
gel filtration
41500
-
isoform III, SDS-PAGE
additional information
-
values between 36000 and 41000, dependent on expression system
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 38200, about, sequence calculation
monomer
additional information
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycoprotein
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
2.95 A under cryoconditions, crystal growing by hanging drop vapor diffusion, 303 K, 0.8 M potassium sodium tartrate tetrahydrate,pH 7.5 - 8.0
-
cocrystallized with inhibitor 6, the complete data are collected to 3.0 A resolution
-
crystals of free STR1 and co-crystallization of STR1 and tryptamine, 2.95 A and 2.38 A under cryoconditions, crystal growing by hanging drop vapor diffusion, 302-304 K, 0.8 M potassium sodium tartrate tetrahydrate, pH 7.5 - 8.0, multiple wavelength anomalous dispersion method
-
crystals of free STR1 and co-crystallization of STR1 with each tryptamine and secologanin, crystal growing by hanging drop vapor diffusion, 302-304 K, 0.8 M potassium sodium tartrate tetrahydrate, pH 7.5 - 8.0, combined multiple wavelength anomalous dispersion and molecular replacement methods
-
the crystal structure of STR1 in complex with strictosidine is solved at a resolution of 3.0 A
-
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
high loss of activity on repeated freezing and thawing
-
immobilized enzyme is more stable to changes in pH and temperature than soluble enzyme
stable on repeated freezing and thawing
-
unstable when highly diluted, 1 M sucrose or 1 mg/ml bovine serum albumin stabilizes activity
-
ORGANIC SOLVENT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
no loss of activity with 5% PEG, dimethylformamide, acetone, ethanol or DMSO
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20, 1 year, no loss of activity
-
-20, several months, no loss of activity
-20C, 1 week, 50% loss of activity
-
-20C, 1000 d, 50% loss of activity
-
-20C, stable for at least 2 months
-
4C, 300 d, 50% loss of activity
-
4C, immobilized enzyme, 2 years, 55% loss of activity
-
4C, partially purified enzyme, stable for more than one week
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
by Ni-NTA affinity chromatography
-
by one-step affinity purification using a amylose column
-
from serum free medium of transformed Sf9 cells
-
hydrophobic interaction chromatography used for purification
Cinchona robusta
-
Ni-NTA column, Mono Q column, concentration to 10 mg/ml in 10 mM Tris-HCl pH 8.0 before crystallization
-
six isoforms purified
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cloned with His-tag, expression in Escherichia coli strain M15, after expression and Ni-NTA column removed by DAPase
-
expressed in Nicotiana plumbaginifolia cultured cells
expressed in Sf9 cells using the Bacullovirus system, enzyme is secreted into the medium
-
expressed in tobacco
-
expression in Escherichia coli M15 cells, functional co-expression with strictosidine glucosidase
-
expression in Escherichia coli, coexpression with chaerone pG-Tf2
-
for expression in Escherichia coli
-
for expression in Escherichia coli BL21DE3 cells
-
functional overexpression of Catharanthus roseus tryptophan decarboxylase and strictosidine synthase in rol gene integrated transgenic hairy root cell suspensions of Vinca minor using sonication-assisted Agrobacterium tumefaciens strain LBA1119 transformation, all the three rol genes, i.e., rol A, rol B, and rol C are used, real-time PCR quantitative expression analysis
-
gene RvSTR, DNA and amino acid sequence determination and analysis, sequence comparison and phylogenetic analysis
gene STR, semiquantitative RT-PCR expression analysis
-
overexpressed in host strain
-
STR gene, expresssion of wild-type enzyme and mutant constructs in Escherichia coli strain BL21(DE3)pLysS
-
subcloned into the pGEM-T Easy vector, excised and ligated into pGAL-MF to obtain pSTSMF-FLAG for expression in Saccharomyces cerevisiae, and into pET28a+ to obtain pSTSMF-HIS for expression in Escherichia coli
-
the four genes SSL4, SSL5, SSL6, and SSL7 are arranged in tandem on chromosome 3, expression analysis, phylogenetic analysis, putative cis-acting DNA elements in the 5'-flanking regions of the four SSL genes, expression and transcription profiling, overview; the four genes SSL4, SSL5, SSL6, and SSL7 are arranged in tandem on chromosome 3, expression analysis, phylogenetic analysis, putative cis-acting DNA elements in the 5'-flanking regions of the four SSL genes, expression and transcription profiling, overview; the four genes SSL4, SSL5, SSL6, and SSL7 are arranged in tandem on chromosome 3, expression analysis, phylogenetic analysis, putative cis-acting DNA elements in the 5'-flanking regions of the four SSL genes, expression and transcription profiling, overview; the four genes SSL4, SSL5, SSL6, and SSL7 are arranged in tandem on chromosome 3, expression analysis, phylogenetic analysis, putative cis-acting DNA elements in the 5'-flanking regions of the four SSL genes, expression and transcription profiling, overview; the four genes SSL4, SSL5, SSL6, and SSL7 are arranged in tandem on chromosome 3, expression analysis, phylogenetic analysis, putative cis-acting DNA elements in the 5'-flanking regions of the four SSL genes, expression and transcription profiling, overview
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
enzyme expression is highly induced by oxidative stress, especially by buthionine sulfoximine-jasmonic acid, and also, to a lesser extent, by jasmonic acid and H2O2
-
high expression in flower, moderate expression in leaf and root, low expression in stem
-
induced expression under plant defense signals such as methyl jasmonate and salicylic acid
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
D177A
-
mutant engineered for redesigning the substrate specificity
E277G
-
mutant engineered for redesigning the substrate specificity
F232T
-
mutant engineered for redesigning the substrate specificity
F314A
-
mutant engineered for redesigning the substrate specificity
F330L
-
mutant engineered for redesigning the substrate specificity
H283A
-
mutant engineered for redesigning the substrate specificity
H313N
-
mutant engineered for redesigning the substrate specificity
L329G
-
mutant engineered for redesigning the substrate specificity
Q282A
-
mutant engineered for redesigning the substrate specificity
S275G
-
mutant engineered for redesigning the substrate specificity
V182G
-
mutant engineered for redesigning the substrate specificity
W153F
-
mutant engineered for redesigning the substrate specificity
Y109H
-
mutant engineered for redesigning the substrate specificity
Y155A
-
mutant engineered for redesigning the substrate specificity
C97S
loss of activity
D213E
loss of activity
D213N
loss of activity
E194D
about 30% of wild-type activity
E194V
about 55% of wild-type activity
H306L
loss of activity
H317L
loss of activity
K144L
about 124% of wild-type activity
K200L
loss of activity
K200R
about 90% of wild-type activity
K236L
loss of activity
K236R
loss of activity
N251S
about 115% of wild-type activity
N88S
loss of activity
Y63F
about 50% of wild-type activity
Y63L
about 50% of wild-type activity
E309A
-
mutant with 25% decrease of kcat
H307A
-
mutant with 130-fold increase of Km for secologanin
Y151F
-
mutant with 2.8-fold increase of Km for tryptamin
biotechnology
the enzyme encoding gene is a candidate gene for metabolic engineering of the TIA pathway in Rauwolfia verticillata
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
biotechnology
medicine
synthesis