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Information on EC 4.3.3.2 - strictosidine synthase
for references in articles please use BRENDA:EC4.3.3.2
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Old data from external sources may still be available.
Please check here for current data: EC 3.5.99.13
Please check here for current data: EC 3.5.99.13
transferred to EC 3.5.99.13, strictosidine synthase
IUBMB Comments
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
strictosidine synthase, ojstr, osstrl2, more
top
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
str
STR1
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PATHWAY SOURCE
PATHWAYS
MetaCyc
secologanin and strictosidine biosynthesis
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
1H-indole-4-ethanamine + secologanin
(S)-1H-azepino-[3,4,5]indolyl-strictosidine
Substrates: -
Products: -
Products: -
?
2-(1H-indol-3-yl)propan-1-amine + secologanin
3alpha-(S)-6-(S)-methylstrictosidine + 3alpha-(S)-6-(R)-methylstrictosidine + H2O
Substrates: 100% activity
Products: -
Products: -
?
2-(2-methyl-1H-indol-3-yl)ethan-1-aminium + secologanin
ternary complex + H2O
-
Substrates: -
Products: -
Products: -
?
2-(4-fluoro-1H-indol-3-yl)propan-1-amine + secologanin
?
Substrates: about 105% activity compared to 2-(1H-indol-3-yl)propan-1-amine
Products: -
Products: -
?
2-(4-methyl-1H-indol-3-yl)propan-1-amine + secologanin
?
Substrates: about 38% activity compared to 2-(1H-indol-3-yl)propan-1-amine
Products: -
Products: -
?
2-(5-fluoro-1H-indol-3-yl)propan-1-amine + secologanin
?
Substrates: about 4% activity compared to 2-(1H-indol-3-yl)propan-1-amine
Products: -
Products: -
?
2-(6-fluoro-1H-indol-3-yl)propan-1-amine + secologanin
?
Substrates: about 7% activity compared to 2-(1H-indol-3-yl)propan-1-amine
Products: -
Products: -
?
2-(7-fluoro-1H-indol-3-yl)propan-1-amine + secologanin
?
Substrates: about 41% activity compared to 2-(1H-indol-3-yl)propan-1-amine
Products: -
Products: -
?
2-(7-methyl-1H-indol-3-yl)propan-1-amine + secologanin
?
Substrates: about 17% activity compared to 2-(1H-indol-3-yl)propan-1-amine
Products: -
Products: -
?
tryptamine + 3-methylbutanal
(1R)-1-(2-methylpropyl)-2,3,4,9-tetrahydro-1H-b-carboline + H2O
tryptamine + hexanal
(1R)-1-pentyl-2,3,4,9-tetrahydro-1H-b-carboline + H2O
-
Substrates: -
Products: -
Products: -
?
additional information
?
-
Substrates: no activity with 2-(5-methyl-1H-indol-3-yl)propan-1-amine and 2-(6-methyl-1H-indol-3-yl)propan-1-amine
Products: -
Products: -
-
3-alpha(S)-strictosidine + H2O
tryptamine + secologanin
Substrates: -
Products: -
Products: -
?
3-alpha(S)-strictosidine + H2O
tryptamine + secologanin
Substrates: -
Products: -
Products: -
r
3-alpha(S)-strictosidine + H2O
tryptamine + secologanin
-
Substrates: -
Products: -
Products: -
r
3-alpha(S)-strictosidine + H2O
tryptamine + secologanin
Substrates: -
Products: -
Products: -
r
3-alpha(S)-strictosidine + H2O
tryptamine + secologanin
Substrates: -
Products: -
Products: -
r
tryptamine + 3-methylbutanal
(1R)-1-(2-methylpropyl)-2,3,4,9-tetrahydro-1H-b-carboline + H2O
Substrates: 63% conversion
Products: -
Products: -
?
tryptamine + 3-methylbutanal
(1R)-1-(2-methylpropyl)-2,3,4,9-tetrahydro-1H-b-carboline + H2O
-
Substrates: -
Products: -
Products: -
?
tryptamine + acetaldehyde
(1R)-1-methyl-2,3,4,9-tetrahydro-1H-b-carboline + H2O
Substrates: 19% conversion
Products: -
Products: -
?
tryptamine + acetaldehyde
(1R)-1-methyl-2,3,4,9-tetrahydro-1H-b-carboline + H2O
-
Substrates: -
Products: -
Products: -
?
tryptamine + butanal
(1R)-1-propyl-2,3,4,9-tetrahydro-1H-b-carboline + H2O
Substrates: 22% conversion
Products: -
Products: -
?
tryptamine + butanal
(1R)-1-propyl-2,3,4,9-tetrahydro-1H-b-carboline + H2O
-
Substrates: -
Products: -
Products: -
?
tryptamine + propanal
(1R)-1-ethyl-2,3,4,9-tetrahydro-1H-b-carboline + H2O
Substrates: 13% conversion
Products: -
Products: -
?
tryptamine + propanal
(1R)-1-ethyl-2,3,4,9-tetrahydro-1H-b-carboline + H2O
-
Substrates: -
Products: -
Products: -
?
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
Substrates: -
Products: -
Products: -
r
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
-
Substrates: -
Products: -
Products: -
r
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
Substrates: -
Products: -
Products: -
?
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
Substrates: -
Products: -
Products: -
r
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
-
Substrates: -
Products: -
Products: -
?
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
Substrates: -
Products: -
Products: -
?
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
Substrates: -
Products: -
Products: -
r
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
Substrates: -
Products: -
Products: -
?
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
-
Substrates: -
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
3-alpha(S)-strictosidine + H2O
tryptamine + secologanin
Substrates: -
Products: -
Products: -
?
3-alpha(S)-strictosidine + H2O
tryptamine + secologanin
Substrates: -
Products: -
Products: -
r
3-alpha(S)-strictosidine + H2O
tryptamine + secologanin
-
Substrates: -
Products: -
Products: -
r
3-alpha(S)-strictosidine + H2O
tryptamine + secologanin
Substrates: -
Products: -
Products: -
r
3-alpha(S)-strictosidine + H2O
tryptamine + secologanin
Substrates: -
Products: -
Products: -
r
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
Substrates: -
Products: -
Products: -
r
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
-
Substrates: -
Products: -
Products: -
r
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
Substrates: -
Products: -
Products: -
?
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
Substrates: -
Products: -
Products: -
r
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
-
Substrates: -
Products: -
Products: -
?
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
Substrates: -
Products: -
Products: -
?
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
Substrates: -
Products: -
Products: -
r
tryptamine + secologanin
3-alpha(S)-strictosidine + H2O
-
Substrates: -
Products: -
Products: -
?
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Infertility, Male
An atypical strictosidine synthase, OsSTRL2, plays key roles in anther development and pollen wall formation in rice.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.101
2-(1H-indol-3-yl)propan-1-amine
wild type enzyme, at pH 7.0 and 28°C
-
1.292
2-(1H-indol-3-yl)propan-1-amine
mutant enzyme Y151F, at pH 7.0 and 28°C
-
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0046
2-(1H-indol-3-yl)propan-1-amine
mutant enzyme Y151F, at pH 7.0 and 28°C
-
8.42
2-(1H-indol-3-yl)propan-1-amine
wild type enzyme, at pH 7.0 and 28°C
-
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0036
2-(1H-indol-3-yl)propan-1-amine
mutant enzyme Y151F, at pH 7.0 and 28°C
-
83.35
2-(1H-indol-3-yl)propan-1-amine
wild type enzyme, at pH 7.0 and 28°C
-
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
metabolism
-
enzyme overexpression in hairy roots constitutively increases the biosynthesis of bioactive Uncaria rhynchophylla monoterpene indole alkaloids (rhynchophylline, isorhynchophylline, corynoxeine, etc.)
metabolism
gate enzyme for monoterpenoid indole alkaloid biosynthesis
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). STSY_CATRO
352
1
39094
Swiss-Prot
Secretory Pathway (Reliability: 3)
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
enzyme in complex with 2-(1H-indol-3-yl)propan-1-amine, hanging drop vapor diffusion method, using 0.8 M potassium sodium tartrate tetrahydrate and 0.1 M HEPES, pH 7.5
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
F226A
the mutant shows about 90% and 57% activity with 2-(1H-indol-3-yl)propan-1-amine and tryptamine, respectively, compared to the wild type enzyme
Y151A
the mutant shows about 2% and 40% activity with 2-(1H-indol-3-yl)propan-1-amine and tryptamine, respectively, compared to the wild type enzyme
Y151F
the mutant shows about 10% and 82% activity with 2-(1H-indol-3-yl)propan-1-amine and tryptamine, respectively, compared to the wild type enzyme
Y151F/F226A
the mutant shows about 5% and 50% activity with 2-(1H-indol-3-yl)propan-1-amine and tryptamine, respectively, compared to the wild type enzyme
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Sheng, X.; Himo, F.
Computational study of Pictet-Spenglerase strictosidine synthase Reaction mechanism and origins of enantioselectivity of natural and non-natural substrates
ACS Catal.
10
13630-13640
2020
Rauvolfia serpentina
-
brenda
Liu, H.; Panjikar, S.; Sheng, X.; Futamura, Y.; Zhang, C.; Shao, N.; Osada, H.; Zou, H.
beta-Methyltryptamine provoking the crucial role of strictosidine synthase Tyr151-OH for its stereoselective Pictet-Spengler reactions to tryptoline-type alkaloids
ACS Chem. Biol.
17
187-197
2022
Rauvolfia serpentina (P68175)
brenda
Guo, E.; Yuan, M.; Xu, L.; Ren, Q.; Wang, Z.; Li, Z.; Wu, Z.; Liu, W.; Zhao, Y.; Feng, F.; Xu, J.
Identification of three key enzymes involved in the biosynthesis of tetracyclic oxindole alkaloids in Uncaria rhynchophylla
Bioorg. Chem.
136
106545
2023
Uncaria rhynchophylla
brenda
Mou, M.; Zhang, C.; Zhang, S.; Chen, F.; Su, H.; Sheng, X.
Uncovering the mechanism of azepino-indole skeleton formation via Pictet-Spengler reaction by strictosidine synthase A quantum chemical investigation
ChemistryOpen
12
e202300043
2023
Rauvolfia serpentina (P68175)
brenda
Cao, N.; Wang, C.H.
Strictosidine synthase, an indispensable enzyme involved in the biosynthesis of terpenoid indole and beta-carboline alkaloids
Chin. J. Nat. Med.
19
591-607
2021
Catharanthus roseus (A0A140DC41), Cinchona pubescens, Ophiorrhiza pumila (Q94LW9), Rauvolfia serpentina (P68175)
brenda
Jiang, C.X.; Yu, J.X.; Fei, X.; Pan, X.J.; Zhu, N.N.; Lin, C.L.; Zhou, D.; Zhu, H.R.; Qi, Y.; Wu, Z.G.
Gene coexpression networks allow the discovery of two strictosidine synthases underlying monoterpene indole alkaloid biosynthesis in Uncaria rhynchophylla
Int. J. Biol. Macromol.
226
1360-1373
2023
Uncaria rhynchophylla
brenda
Eger, E.; Simon, A.; Sharma, M.; Yang, S.; Breukelaar, W.B.; Grogan, G.; Houk, K.N.; Kroutil, W.
Inverted binding of non-natural substrates in strictosidine synthase leads to a switch of stereochemical outcome in enzyme-catalyzed Pictet-Spengler reactions
J. Am. Chem. Soc.
142
792-800
2020
Ophiorrhiza pumila (Q94LW9)
brenda
Kulhar, N.; Rajakumara, E.
Binding order and apparent binding affinity in the bisubstrate activity of strictosidine synthase
J. Biomol. Struct. Dyn.
21
1-13
2023
Rauvolfia serpentina
brenda
Sahay, A.; Piprodhe, A.; Pise, M.
In silico analysis and homology modeling of strictosidine synthase involved in alkaloid biosynthesis in Catharanthus roseus
J. Genet. Eng. Biotechnol.
18
44
2020
Catharanthus roseus (P18417)
brenda
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