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
4.3.3.2
-
RECOMMENDED NAME
GeneOntology No.
strictosidine synthase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
3-alpha(S)-strictosidine + H2O = tryptamine + secologanin
show the reaction diagram
-
-
-
-
3-alpha(S)-strictosidine + H2O = tryptamine + secologanin
show the reaction diagram
catalytic reaction mechanism
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
condensation
-
Pictet-Spengler condensation between tryptamine and secologanin
condensation
-
Pictet-Spengler condensation between tryptamine and secologanin
condensation of aldehyde function with amine function
-
-
-
-
Pictete-Spengler reaction
P18417
-
Pictete-Spengler reaction
-
-
PATHWAY
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.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SSL
-, Q9CAZ7, Q9SD04, Q9SD05, Q9SD07
-
str
Q94LW9
-
STR1
P18417
-
stricotsidine synthase
P68175
-
strictosidine synthase
-
-
strictosidine synthase
-
-
strictosidine synthase
-
-
strictosidine synthase-like protein
-, Q9CAZ7, Q9SD04, Q9SD05, Q9SD07
-
CAS REGISTRY NUMBER
COMMENTARY
69669-72-3
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
Amsonia salicifolia
-
-
-
Manually annotated by BRENDA team
ecotype Columbia-0, gene SSL4 or At3g51420; ecotype Columbia-0, gene SSL5 or At3g51430
-
-
Manually annotated by BRENDA team
gene SSL4, At3g51420; ecotype Columbia-0, gene SSL4
UniProt
Manually annotated by BRENDA team
gene SSL5 or YSL2, At3g51430; ecotype Columbia-0, gene SSL5
UniProt
Manually annotated by BRENDA team
gene SSL6, At3g51440; ecotype Columbia-0, gene SSL6
UniProt
Manually annotated by BRENDA team
gene SSL7, At3g51450; ecotype Columbia-0, gene SSL7
UniProt
Manually annotated by BRENDA team
Catharanthus pusillus
-
-
-
Manually annotated by BRENDA team
i.e. Vinca rosea
-
-
Manually annotated by BRENDA team
transformed with Agrobacterium tumefaciens to enable growth in the absence of exogenous plant growth regulators
UniProt
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
Stemmadenia tomentosa var. palmeri
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
physiological function
-
involved in biosynthesis of monoterpenoid indole alkaloids
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
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
P18417
-
-
-
?
3-alpha(S)-strictosidine + H2O
tryptamine + secologanin
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
P18417
-
-
-
?
4-methyltryptamine + secologanin
4-methyl-3-alpha(S)-strictosidine + H2O
show the reaction diagram
P18417
-
-
-
?
4-methyltryptamine + secologanin
? + H2O
show the reaction diagram
Q94LW9
poor substrate
-
-
?
5,6-dihydroxytryptamine
?
show the reaction diagram
P68175
-
-
-
?
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
P68175
-
-
-
?
5-fluorotryptamine + secologanin
?
show the reaction diagram
-
6% of the activity with trypamine
-
-
?
5-fluorotryptamine + secologanin
5-fluoro-3-alpha(S)-strictosidine + H2O
show the reaction diagram
-
-
-
-
?
5-fluorotryptamine + secologanin
5-fluoro-3-alpha(S)-strictosidine + H2O
show the reaction diagram
P18417
-
-
-
?
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
Q94LW9
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
Q94LW9
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
P68175
-
-
-
?
6-fluorotryptamine + secologanin
6-fluoro-3-alpha(S)-strictosidine + H2O
show the reaction diagram
-
-
-
-
?
6-fluorotryptamine + secologanin
6-fluoro-3-alpha(S)-strictosidine + H2O
show the reaction diagram
P18417
-
-
-
?
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
P68175
-
-
-
?
6-methoxytryptamine + secologanin
? + H2O
show the reaction diagram
Q94LW9
poor substrate
-
-
?
6-methyl-tryptamine + H2O
?
show the reaction diagram
-
-
-
-
?
6-methyltryptamine + secologanin
6-methyl-3-alpha(S)-strictosidine + H2O
show the reaction diagram
-
-
-
-
?
6-methyltryptamine + secologanin
6-methyl-3-alpha(S)-strictosidine + H2O
show the reaction diagram
P18417
-
-
-
?
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
?
show the reaction diagram
-
8% of the activity with trypamine
-
-
?
7-fluorotryptamine + secologanin
7-fluoro-3-alpha(S)-strictosidine + H2O
show the reaction diagram
P18417
-
-
-
?
7-methyltryptamine
?
show the reaction diagram
P68175
-
-
-
?
7-methyltryptamine + secologanin
?
show the reaction diagram
-
15% of the activity with trypamine
-
-
?
7-methyltryptamine + secologanin
7-methyl-3-alpha(S)-strictosidine + H2O
show the reaction diagram
-
-
-
-
?
7-methyltryptamine + secologanin
7-methyl-3-alpha(S)-strictosidine + H2O
show the reaction diagram
P18417
-
-
-
?
7-methyltryptamine + secologanin
? + H2O
show the reaction diagram
Q94LW9
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
-
-
?
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
P68175
-
-
-
?
serotonin + secologanin
5-hydroxy-3-alpha(S)-strictosidine + H2O
show the reaction diagram
-
-
-
-
?
serotonin + secologanin
5-hydroxy-3-alpha(S)-strictosidine + H2O
show the reaction diagram
P18417
-
-
-
?
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
Cinchona robusta
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
P18417
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
Amsonia salicifolia
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
Amsonia salicifolia
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
Stemmadenia tomentosa var. palmeri
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
Stemmadenia tomentosa var. palmeri
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
highly specific
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
higher activity in dark grown than in light grown cultures
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
Cinchona robusta
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
P18417
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
Amsonia salicifolia
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
Amsonia salicifolia
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
Stemmadenia tomentosa var. palmeri
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
Stemmadenia tomentosa var. palmeri
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
P18417
the enzyme catalyses the biological Pictete-Spengler reaction of tryptamine and secologanin
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
the enzyme catalyses the biological Pictete-Spengler reaction of tryptamine and secologanin. Tryptamine is located at the bottom of the substrate binding pocket, where its primary amine group is connected with residue Glu309 by a hydrogen bond. The main amino acid residues involved in forming the active centre are Tyr105, Trp149, Val167, Met180, Val208, Phe226, Ser269, Met276, His277, His307, Phe308, Glu309, Leu323, and Phe324
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
show the reaction diagram
-
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
show the reaction diagram
Q1L6F4
the strictosidine synthase catalyzes the condensation of tryptamine and secologanin to form strictosidine, which is the universal precursor for a wide range of pharmaceutical terpenoid indole alkaloids, TIA, e.g. in biosynthesis of reserpine and ajmalicine from the Chinese native TIAs-producing plant, overview
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
show the reaction diagram
-
the strictosidine synthase plays a central role in the biosynthesis of all structural types of monoterpenoid indole alkaloids, overview
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
show the reaction diagram
P18417
the strictosidine synthase plays a central role in the biosynthesis of all structural types of monoterpenoid indole alkaloids, overview
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
show the reaction diagram
Q1L6F4
the unique essential and conserved catalytic residue is Glu309
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
show the reaction diagram
-
assay at pH 7.0, 28C, reaction stopped by adding methanol
-
-
?
tryptamine + secologanin
3alpha(S)-strictosidine
show the reaction diagram
-
-
-
-
?
tryptamine + secologanin
3alpha(S)-strictosidine
show the reaction diagram
P68175
-
-
-
?
tryptamine + secologanin
? + H2O
show the reaction diagram
Q94LW9
poor substrate
-
-
?
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
-
-
?
additional information
?
-
-
5-methoxytryptamine is not utilized
-
-
-
additional information
?
-
-
tryptophan, phenylethylamine, tyramine and pyrrole cannot subsitute for tryptamine, overview on substituted tryptamines
-
-
-
additional information
?
-
P18417
substrate specificity, e.g. with tryptamine derivatives, overview. No activity with 2-pyrrole-3-ethylamine, phenylethylamine, tyramine, homoveratrylamine, N-acetyl-5-hydroxytryptamine, N-methyltryptamine, 3-methylamine indole, 3-propylamine indole, 2-methyltryptamine, 2-ethyltryptamine, 5,6-dihydroxytryptamine, 5,7-dimethoxytryptamine, histamine, dopamine, 5-methyltryptamine, 6-methyltryptamine, and 5-methoxytryptamine, overview
-
-
-
additional information
?
-
-
substrate specificity, e.g. with tryptamine derivatives, overview. No activity with N-acetyl-5-hydroxytryptamine, N-methyltryptamine, N-omega-methyltryptamine, 2-methyl,5-hydroxytryptamine, 3-methylamine indole, 3-propylamine indole, 2-methyltryptamine, 2-ethyltryptamine, 5,7-dimethoxytryptamine, phenylalanine, histamine, dopamine, 5-methyltryptamine, 5-methoxytryptamine, 4,5-dimethyltryptamine, and 4-methyl-5-methoxytryptamine, and with secologanic acid, tarennoside, 18-n-butylsecologanin, and 18-tert-butylsecologanin, overview. Dihydrosecologanin and secologanin acid ethyl ester are poor substrates
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
3-alpha(S)-strictosidine + H2O
tryptamine + secologanin
show the reaction diagram
-
-
-
-
?
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
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
higher activity in dark grown than in light grown cultures
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
Cinchona robusta
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
P18417
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
Amsonia salicifolia
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
Amsonia salicifolia
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
Stemmadenia tomentosa var. palmeri
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
Stemmadenia tomentosa var. palmeri
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
-
involved in synthesis of monoterpenoid indole alkaloides
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
show the reaction diagram
Q1L6F4
the strictosidine synthase catalyzes the condensation of tryptamine and secologanin to form strictosidine, which is the universal precursor for a wide range of pharmaceutical terpenoid indole alkaloids, TIA, e.g. in biosynthesis of reserpine and ajmalicine from the Chinese native TIAs-producing plant, overview
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
show the reaction diagram
-
the strictosidine synthase plays a central role in the biosynthesis of all structural types of monoterpenoid indole alkaloids, overview
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
show the reaction diagram
P18417
the strictosidine synthase plays a central role in the biosynthesis of all structural types of monoterpenoid indole alkaloids, overview
-
-
?
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
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
-
-
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
-
inhibitory above 0.7 mM
tryptamine
-
inhibitory above 1.2 mM
tryptamine
-
inhibitory above 1 mM, soluble and immobilized enzyme
Dinitrofluorobenzene
-
5 mM, no inactivation after 30 min and 15% inactivation after 120 min in Tris-HCl, pH 8.0
-
additional information
-
no inhibition with secologanin
-
additional information
Cinchona robusta
-
no substrate inhibition
-
additional information
-
no substrate inhibition
-
additional information
-
no substrate inhibition
-
additional information
-
no inactivation by phenylmethanesulfonyl fluoride, L-chloro-3-(4-tosyl-amido)-4-phenyl-2-butanone and L-chloro-3-(4-tosyl-amido)-7-amino-2-heptanone after 30 and 120 min in 100 mM potassium phosphate buffer, pH 7.0
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
Bovine serum albumin
-
1 mg/ml stimulates activity
-
additional information
-, Q9CAZ7, Q9SD04, Q9SD05, Q9SD07
gene SSL5 is induced to various degrees by plant defence signalling compounds, such as salicylic acid, methyl jasmonate and ethylene, as well as by wounding and exposure to the plant pathogens Alternaria brassicicola and cucumber mosaic virus, overview; gene SSL5 is induced to various degrees by plant defence signalling compounds, such as salicylic acid, methyl jasmonate and ethylene, as well as by wounding and exposure to the plant pathogens Alternaria brassicicola and cucumber mosaic virus, overview; gene SSL6 is induced to various degrees by plant defence signalling compounds, such as salicylic acid, methyl jasmonate and ethylene, as well as by wounding and exposure to the plant pathogens Alternaria brassicicola and cucumber mosaic virus, overview; the AtSSL4 gene is constitutively expressed and not significantly induced by any treatment, e.g. no induction by salicylic acid, methyl jasmonate and ethylene, as well as by wounding and exposure to the plant pathogens Alternaria brassicicola and cucumber mosaic virus; the AtSSL4 gene is constitutively expressed and not significantly induced by any treatment, while the other three AtSSL genes are induced to various degrees by plant defence signalling compounds, such as salicylic acid, methyl jasmonate and ethylene, as well as by wounding and exposure to the plant pathogens Alternaria brassicicola and cucumber mosaic virus; the gene SSL4 is constitutively expressed and not significantly induced by any treatment, e.g. with plant defence signalling compounds, such as salicylic acid, methyl jasmonate and ethylene, or by wounding and exposure to the plant pathogens Alternaria brassicicola and cucumber mosaic virus
-
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
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
-
5-fluoro-tryptamine
-
wild-type enzyme
1.302
-
5-fluoro-tryptamine
-
mutant V208A
0.844
-
5-hydroxy-tryptamine
-
mutant V208A
2.255
-
5-hydroxy-tryptamine
-
wild-type enzyme
3.592
-
5-methoxy-tryptamine
-
mutant V208A
0.281
-
5-methyl-tryptamine
-
mutant V208A
0.37
-
5-methyltryptamine
-
mutant V214M
0.136
-
6-fluoro-tryptamine
-
wild-type enzyme
0.356
-
6-fluoro-tryptamine
-
mutant V208A
0.307
-
6-methoxy-tryptamine
-
mutant V208A
0.962
-
6-methoxy-tryptamine
-
wild-type enzyme
0.393
-
6-methyl-tryptamine
-
wild-type enzyme
0.762
-
6-methyl-tryptamine
-
mutant V208A
3.5
-
dihydrosecologanin
-
pH 7.0, 35C
0.039
-
secologanin
-
wild type, pH 7.0, 35C, 15 min
0.044
-
secologanin
-
Y151F, pH 7.0, 35C, 15 min
0.095
-
secologanin
-
E309A, pH 7.0, 35C, 15 min
0.46
-
secologanin
-
pH 7.5, 30C
0.9
-
secologanin
-
hairy root enzyme, 37C
1
-
secologanin
-
-
2.1
-
secologanin
-
immobilized enzyme, pH 6.5, 37C
2.6
-
secologanin
-
pH 7.0, 35C
3.4
-
secologanin
-
pH 7.0, 35C
3.4
-
secologanin
-
soluble enzyme, pH 6.5, 37C
4
-
secologanin
-
-
5.07
-
secologanin
-
H307A, pH 7.0, 35C, 15 min
1.036
-
serotonin
-
wild-type enzyme
0.0014
-
tryptamine
-
wild-type strictosidine synthase expressed in yeast
0.002
-
tryptamine
Cinchona robusta
-
isoform I b
0.003
-
tryptamine
Cinchona robusta
-
isoform II b
0.0054
-
tryptamine
-
E309A, pH 7.0, 35C, 15 min
0.0062
-
tryptamine
-
wild type, pH 7.0, 35C, 15 min
0.007
-
tryptamine
P18417
-
0.0074
-
tryptamine
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
0.0079
-
tryptamine
-
H307A, pH 7.0, 35C, 15 min
0.008
-
tryptamine
Cinchona robusta
-
isoform I a
0.009
-
tryptamine
-
pH 6.8, 30C
0.015
-
tryptamine
Cinchona robusta
-
isoform II a
0.0172
-
tryptamine
-
Y151F, pH 7.0, 35C, 15 min
0.072
-
tryptamine
-
wild-type enzyme
0.219
-
tryptamine
-
mutant V208A
0.42
-
tryptamine
-
mutant V214M
0.44
-
tryptamine
-
mutant E315A
0.5
-
tryptamine
-
hairy root enzyme, 37C
0.62
-
tryptamine
-
mutant F232L
0.83
-
tryptamine
-
pH 7.5, 30C
0.9
-
tryptamine
-
immobilized enzyme, pH 6.5, 37C
1
-
tryptamine
-
-
2.3
-
tryptamine
-
pH 7.0, 35C
2.3
-
tryptamine
-
soluble enzyme, pH 6.5, 37C
4
-
tryptamine
-
-
5.8
-
tryptamine
-
pH 7.0, 35C
TURNOVER NUMBER [1/s]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.058
-
2-(4-fluoro-1H-indol-3-yl)ethanamine
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
0.0031
-
2-(4-methyl-1H-indol-3-yl)ethanamine
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
0.0072
-
2-(5-fluoro-1H-indol-3-yl)ethanamine
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
0.0093
-
2-(6-fluoro-1H-indol-3-yl)ethanamine
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
0.0018
-
2-(7-fluoro-1H-indol-3-yl)ethanamine
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
0.0048
-
2-(7-methyl-1H-indol-3-yl)ethanamine
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
0.0038
-
2-benzofuran-3-yl-ethylamine
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
0.0016
-
3-(2-aminoethyl)-1H-indol-5-ol
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
3.4
-
5-fluoro-tryptamine
-
wild-type enzyme
3.8
-
5-fluoro-tryptamine
-
mutant V208A
21.24
-
5-fluoro-tryptamine
-
mutant V208A
37.46
-
5-fluoro-tryptamine
-
wild-type enzyme
0.025
-
5-hydroxy-tryptamine
-
wild-type enzyme
0.99
-
5-hydroxy-tryptamine
-
mutant V208A
18.12
-
5-hydroxy-tryptamine
-
mutant V208A
562.1
-
5-hydroxy-tryptamine
-
wild-type enzyme
0.21
-
5-methoxy-tryptamine
-
mutant V208A
79.66
-
5-methoxy-tryptamine
-
mutant V208A
0.03
0.55
5-methyl-tryptamine
-
mutant V208A
6.56
-
5-methyl-tryptamine
-
mutant V208A
0.52
-
6-fluoro-tryptamine
-
mutant V208A
13.63
-
6-fluoro-tryptamine
-
mutant V208A
16.9
-
6-fluoro-tryptamine
-
wild-type enzyme
23.37
-
6-fluoro-tryptamine
-
wild-type enzyme
0.97
-
6-methoxy-tryptamine
-
mutant V208A
5.32
-
6-methoxy-tryptamine
-
wild-type enzyme
16.66
-
6-methoxy-tryptamine
-
mutant V208A
0.057
0.65
6-methyl-tryptamine
-
mutant V208A
2.32
-
6-methyl-tryptamine
-
wild-type enzyme
10.95
-
6-methyl-tryptamine
-
mutant V208A
4.5
-
secologanin
-
in reaction with tryptamine
11.13
-
serotonin
-
wild-type enzyme
0.002
-
tryptamine
P18417
-
0.015
-
tryptamine
-
HPLC, neutral pH, micromolar to low millimolar substrate concentrations
0.057
0.65
tryptamine
-
wild-type enzyme
0.64
-
tryptamine
-
mutant V208A
1.3
-
tryptamine
-
wild-type strictosidine synthase expressed in yeast
10.65
-
tryptamine
-
wild-type enzyme
11.31
-
tryptamine
-
mutant V208A
54.09
-
tryptamine
-
mutant V208A
Ki VALUE [mM]
Ki VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.007
-
Quinine
Cinchona robusta
-
-
IC50 VALUE [mM]
IC50 VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
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
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
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
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
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
6.8
-
-
soluble enzyme
6.8
-
-
HPLC activity assay
6.9
-
Catharanthus pusillus
-
-
7
-
-
activity assay
7
-
-
activity assay
7
-
-
assay at
pH RANGE
pH RANGE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
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
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
28
-
-
assay at
30
-
-
HPLC activity assay
45
50
Amsonia salicifolia
-
-
45
-
Amsonia salicifolia, Amsonia tabernaemontana, Catharanthus longifolius, Catharanthus pusillus, Catharanthus roseus, Catharanthus trichophyllus, Ervatamia divaricatum, Ochrosia elliptica, Rauvolfia verticillata, Stemmadenia tomentosa var. palmeri, Vinca major, Vinca minor
-
-
pI VALUE
pI VALUE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
5.19
-
Q1L6F4
sequence calculation
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
Amsonia orientalis, Amsonia salicifolia, Ochrosia elliptica, Rauvolfia vomitoria, Stemmadenia tomentosa var. palmeri, Vinca major, Voacanga africana
-
-
Manually annotated by BRENDA team
Cinchona robusta
-
-
Manually annotated by BRENDA team
-
of aerial organs. Coexpression of strictosidine synthase and strictosidine beta-D-glucosidase in the epidermal first barrier
Manually annotated by BRENDA team
Q94LW9
hairy root and root, high expression
Manually annotated by BRENDA team
Q94LW9
hairy root and root, high expression
Manually annotated by BRENDA team
Q94LW9
high expression
Manually annotated by BRENDA team
additional information
-
no activity in leaf and callus
Manually annotated by BRENDA team
additional information
-, Q9CAZ7, Q9SD04, Q9SD05, Q9SD07
gene SSL5 is induced to various degrees by plant defence signalling compounds, such as salicylic acid, methyl jasmonate and ethylene, as well as by wounding and exposure to the plant pathogens Alternaria brassicicola and cucumber mosaic virus, overview; gene SSL5 is induced to various degrees by plant defence signalling compounds, such as salicylic acid, methyl jasmonate and ethylene, as well as by wounding and exposure to the plant pathogens Alternaria brassicicola and cucumber mosaic virus, overview; gene SSL5 is induced to various degrees by plant defence signalling compounds, such as salicylic acid, methyl jasmonate and ethylene, as well as by wounding and exposure to the plant pathogens Alternaria brassicicola and cucumber mosaic virus, overview; gene SSL6 is induced to various degrees by plant defence signalling compounds, such as salicylic acid, methyl jasmonate and ethylene, as well as by wounding and exposure to the plant pathogens Alternaria brassicicola and cucumber mosaic virus, overview; the gene SSL4 is constitutively expressed and not significantly induced by any treatment, e.g. with plant defence signalling compounds, such as salicylic acid, methyl jasmonate and ethylene, or by wounding and exposure to the plant pathogens Alternaria brassicicola and cucumber mosaic virus
Manually annotated by BRENDA team
additional information
Q1L6F4
tissue expression pattern analysis, overview
Manually annotated by BRENDA team
additional information
-
no expression in laticifer-idioblast CrD4H-expressing cells
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
30000
-
-
gel filtration
31000
-
-
isoform III, gel filtration
33000
-
Cinchona robusta
-
SDS-PAGE, isoform I b and II b
34000
-
-
gel filtration
35000
-
-
SDS-PAGE
35000
-
Cinchona robusta
-
SDS-PAGE, isoforms I a and II a
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 ACCESSION NO.
COMMENTARY
LITERATURE
?
Q1L6F4
x * 38200, about, sequence calculation
monomer
Amsonia orientalis, Amsonia salicifolia, Ochrosia elliptica, Rauvolfia vomitoria, Stemmadenia tomentosa var. palmeri, Vinca major, Voacanga africana
-
-
monomer
-
1 * 35000, SDS-PAGE
additional information
-
the overall enzyme structure of STR1 represents a beta-propeller comprising 6 blades, which are radially arranged around a central 6fold pseudo-symmetry axis, containing three helices in the STR1 structure. Each propeller blade contains four beta-strands, which form a twisted, antiparallel beta-sheet, important role of covalently bound cysteine residues in the integrity of the substrate binding site and in the enzyme's overall structure, structure analysis, overview
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
glycoprotein
-
-
glycoprotein
-
all isoforms, mannose bound to enzyme
glycoprotein
Cinchona robusta
-
all isoforms
glycoprotein
-
glucose, mannose and xylose bound to enzyme
Crystallization/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
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
TEMPERATURE STABILITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
37
-
-
immobilized enzyme, half life: 68 d, 6% of initial activity after one year
37
-
-
immobilized enzyme, half life: 100 d
GENERAL STABILITY
ORGANISM
UNIPROT ACCESSION NO.
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
-
immobilized enzyme is more stable to changes in pH and temperature than soluble enzyme
-
ORGANIC SOLVENT
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
additional information
-
no loss of activity with 5% PEG, dimethylformamide, acetone, ethanol or DMSO
STORAGE STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
-20, several months, no loss of activity
Amsonia orientalis, Amsonia salicifolia
-
-20, 1 year, no loss of activity
-
-20, several months, no loss of activity
-
-20C, 1 week, 50% loss of activity
-
-20C, stable for at least 2 months
-
4C, immobilized enzyme, 2 years, 55% loss of activity
-
4C, partially purified enzyme, stable for more than one week
-
-20, several months, no loss of activity
-
-20C, 1000 d, 50% loss of activity
-
4C, 300 d, 50% loss of activity
-
-20, several months, no loss of activity
Rauvolfia vomitoria, Stemmadenia tomentosa var. palmeri, Vinca major, Voacanga africana
-
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
by one-step affinity purification using a amylose column
-
six isoforms purified
-
hydrophobic interaction chromatography used for purification
Cinchona robusta
-
by Ni-NTA affinity chromatography
-
from serum free medium of transformed Sf9 cells
-
Ni-NTA column, Mono Q column, concentration to 10 mg/ml in 10 mM Tris-HCl pH 8.0 before crystallization
-
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
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
-, Q9CAZ7, Q9SD04, Q9SD05, Q9SD07
expressed in Nicotiana plumbaginifolia cultured cells
-
expressed in tobacco
-
for expression in Escherichia coli BL21DE3 cells
-
overexpressed in host strain
-
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
-
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
-
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
-
gene RvSTR, DNA and amino acid sequence determination and analysis, sequence comparison and phylogenetic analysis
Q1L6F4
EXPRESSION
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
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 ACCESSION NO.
COMMENTARY
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
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
Q94LW9
loss of activity
D213E
Q94LW9
loss of activity
D213N
Q94LW9
loss of activity
E194D
Q94LW9
about 30% of wild-type activity
E194V
Q94LW9
about 55% of wild-type activity
H306L
Q94LW9
loss of activity
H317L
Q94LW9
loss of activity
K144L
Q94LW9
about 124% of wild-type activity
K200L
Q94LW9
loss of activity
K200R
Q94LW9
about 90% of wild-type activity
K236L
Q94LW9
loss of activity
K236R
Q94LW9
loss of activity
N251S
Q94LW9
about 115% of wild-type activity
N88S
Q94LW9
loss of activity
Y63F
Q94LW9
about 50% of wild-type activity
Y63L
Q94LW9
about 50% of wild-type activity
E309A
-
mutant with 25% decrease of kcat
H307A
-
mutant with 130-fold increase of Km for secologanin
V208A
-
Val208 plays a critical role in substrate recognition at the indole moiety of strictosidine
V208A
-
the mutant shows altered substrate specificity compared to the wild-type enzyme, e.g. increased activity with tryptamine, overview
Y151F
-
mutant with 2.8-fold increase of Km for tryptamin
biotechnology
Q1L6F4
the enzyme encoding gene is a candidate gene for metabolic engineering of the TIA pathway in Rauwolfia verticillata
L329G
-
mutant engineered for redesigning the substrate specificity
additional information
-
in a rational redesign approach all 20 naturally occuring amino acids at selected residues in the tryptamine-binding pocket are probed
APPLICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
synthesis
-
decreased production of campothecin on subculturing due to a cross-species biosynthetic pathway is where the endophyte Fusarium solani utilizes indigenous geraniol 10-hydroxylase, secologanin synthase, and tryptophan decarboxylase to biosynthesize precursors. Fusarium solani requires host Campotheca acuminata strictosidine synthase in order to form strictosidine. Biosynthetic genes of campothecin in the seventh subculture generation of the endophyte reveal random and unpredictable nonsynonymous mutations. These random base substitutions lead to dysfunction at the amino acid level. The controls, Top1 gene and rDNA, remained intact over subculturing
biotechnology
-
redesigning the substrate specificity of strictosidine synthase is an important step toward re-engineering the TIA pathway to produce products with novel or improved biological properties
biotechnology
-
modulating the substrate specificity of strictosidine synthase is a critical step toward indole alkaloid pathway engineering to yield nonnatural alkaloids
synthesis
-
immobilized enzyme can be used to synthesize large quantities of 3-alpha(S)-strictosidine, that is a common intermediate in the biosynthesis of indole alkaloids
medicine
-
anti-cancer and anti-hypertensive agents
synthesis
Q94LW9
production of campothecin in hairy root culture of Ophiorrhiza pumila by infection with Agrobacterium tumefaciens. The culture also produces a high level of anthraquinones besides camptothecin. Camptothecin is present not only in hairy root cells, but excreted out to medium at a substantial amount. Camptothecin content in the medium is increased by the presence of a polystyrene resin that absorbs camptothecin
medicine
-
anti-arrhythmic ajmaline agents
medicine
-
anti-cancer, anti-hypertensive, anti-malaria and anti-arrhythmic ajmaline agents
medicine
-
anti-arrhythmic heart disorders, ajmaline agents
synthesis
-
involved in the biosynthesis of almost all plant monoterpenoid indole alkaloids