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Information on EC 4.3.3.2 - strictosidine synthase and Organism(s) Catharanthus roseus and UniProt Accession P18417

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EC Tree
     4 Lyases
         4.3 Carbon-nitrogen lyases
             4.3.3 Amine-lyases
                4.3.3.2 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.
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This record set is specific for:
Catharanthus roseus
UNIPROT: P18417
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The taxonomic range for the selected organisms is: Catharanthus roseus
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
strictosidine synthase, ojstr, osstrl2, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
strictosidine synthase
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Pictete-Spengler reaction
-
condensation
-
Pictet-Spengler condensation between tryptamine and secologanin
condensation of aldehyde function with amine function
-
-
-
-
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
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
3-(2-aminoethyl)-benzothiophene + secologanin
? + H2O
show the reaction diagram
-
-
-
?
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
-
-
-
?
5-fluorotryptamine + secologanin
5-fluoro-3-alpha(S)-strictosidine + H2O
show the reaction diagram
-
-
-
?
6-fluorotryptamine + secologanin
6-fluoro-3-alpha(S)-strictosidine + H2O
show the reaction diagram
-
-
-
?
6-methyltryptamine + secologanin
6-methyl-3-alpha(S)-strictosidine + H2O
show the reaction diagram
-
-
-
?
7-fluorotryptamine + secologanin
7-fluoro-3-alpha(S)-strictosidine + H2O
show the reaction diagram
-
-
-
?
7-methyltryptamine + secologanin
7-methyl-3-alpha(S)-strictosidine + H2O
show the reaction diagram
-
-
-
?
serotonin + secologanin
5-hydroxy-3-alpha(S)-strictosidine + 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
the strictosidine synthase plays a central role in the biosynthesis of all structural types of monoterpenoid indole alkaloids, overview
-
-
?
(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
-
-
?
3-alpha(S)-strictosidine + H2O
tryptamine + secologanin
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-fluorotryptamine + secologanin
?
show the reaction diagram
-
6% of the activity with trypamine
-
-
?
5-hydroxytryptamine + secologanin
?
show the reaction diagram
-
4% of the activity with trypamine
-
-
?
5-methyltryptamine + H2O
?
show the reaction diagram
-
substrate for discovery of active mutants
-
-
?
6-hydroxytryptamine + secologanin
?
show the reaction diagram
-
9% of the activity with trypamine
-
-
?
7-fluorotryptamine + secologanin
?
show the reaction diagram
-
8% of the activity with trypamine
-
-
?
7-methyltryptamine + secologanin
?
show the reaction diagram
-
15% of the activity with trypamine
-
-
?
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
-
-
?
tryptamine + 2'-O-methylsecologanin
?
show the reaction diagram
-
-
-
-
?
tryptamine + 3'-O-methylsecologanin
?
show the reaction diagram
-
-
-
-
?
tryptamine + dihydrosecologanin
?
show the reaction diagram
-
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
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
the strictosidine synthase plays a central role in the biosynthesis of all structural types of monoterpenoid indole alkaloids, overview
-
-
?
3-alpha(S)-strictosidine + H2O
tryptamine + secologanin
show the reaction diagram
-
-
-
-
?
tryptamine + secologanin
3-alpha(S)-strictosidine
show the reaction diagram
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3-[(tert-butoxycarbonyl)amino]propyl (3R,4S)-3-ethenyl-2-(beta-D-glucopyranosyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate
-
-
p-chloromercuribenzoate
-
-
tryptamine
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
bovine serum albumin
-
1 mg/ml stimulates activity
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.007
tryptamine
-
0.94
(2'R)-tryptophanol
-
mutant F232L
8
3'-O-methylsecologanin
-
pH 7.0, 35°C
0.37
5-methyltryptamine
-
mutant V214M
3.5
dihydrosecologanin
-
pH 7.0, 35°C
0.46 - 3.4
secologanin
0.0014 - 2.3
tryptamine
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.002
tryptamine
-
1.3
tryptamine
-
wild-type strictosidine synthase expressed in yeast
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, 30°C
1.07
-
purified enzyme, pH 7.0, 35°C
2.18
-
purified enzyme, pH 6.5
31.62
-
purified enzyme, pH 6.8, 30°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.4
-
immobilized enzyme
7
-
activity assay
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
3 - 9
-
immobilized enzyme
4 - 8.5
-
soluble enzyme
5 - 7.5
-
50% activity
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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
additional information
-
no expression in laticifer-idioblast CrD4H-expressing cells
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
the enzyme is involved in terpenoid indole alkaloid biosynthetic pathway
additional information
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
STSY_CATRO
352
1
39094
Swiss-Prot
Secretory Pathway (Reliability: 1)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
31000
-
isoform III, gel filtration
34000
-
gel filtration
37000
-
determined by SDS-PAGE
38000
-
gel filtration
41500
-
isoform III, SDS-PAGE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycoprotein
PROTEIN VARIANTS
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
additional information
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
-
immobilized enzyme, half life: 68 d, 6% of initial activity after one year
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
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°, 1 year, no loss of activity
-
-20°, several months, no loss of activity
-
-20°C, 1 week, 50% loss of activity
-
-20°C, stable for at least 2 months
-
4°C, immobilized enzyme, 2 years, 55% loss of activity
-
4°C, partially purified enzyme, stable for more than one week
-
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
by one-step affinity purification using a amylose column
-
six isoforms purified
-
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
cooverexpression of geraniol-10-hydroxylase and strictosidine synthase in Ophiorrhiza pumila
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
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
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
significant upregulation in salicylic acid treatment (foliar application of 0.01 and 0.1 mM salicylic acid). Upregulation can result in a higher production rate of vinblastine and vincristine alkaloids
upregulated in plants inoculated with endophytes
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
drug development
cooverexpression of geraniol-10-hydroxylase and strictosidine synthase improves anti-cancer drug camptothecin accumulation in Ophiorrhiza pumila
pharmacology
cooverexpression of geraniol-10-hydroxylase and strictosidine synthase improves anti-cancer drug camptothecin accumulation in Ophiorrhiza pumila
synthesis
overexpression of tryptophan decarboxylase and strictosidine synthase enhances terpenoid indole alkaloid pathway activity and antineoplastic vinblastine biosynthesis in Catharanthus roseus. Vinblastine and vincristine are highly expensive antineoplastic molecules
biotechnology
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
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Treimer, J.F.; Zenk, M.H.
Purification and properties of strictosidine synthase, the key enzyme in indole alkaloid formation
Eur. J. Biochem.
101
225-233
1979
Amsonia orientalis, Amsonia salicifolia, Amsonia tabernaemontana, Catharanthus longifolius, Catharanthus pusillus, Catharanthus roseus, Catharanthus trichophyllus, Ervatamia divaricatum, Ochrosia elliptica, Rauvolfia verticillata, Rauvolfia vomitoria, Stemmadenia tomentosa var. palmeri, Vinca major, Vinca minor, Voacanga africana
Manually annotated by BRENDA team
Mizukami, H.; Nordlov, H.; Lee, S.L.; Scott, A.I.
Purification and properties of strictosidine synthetase (an enzyme condensing tryptamine and secologanin) from Catharanthus roseus cultured cell
Biochemistry
18
3760-3763
1979
Catharanthus roseus
Manually annotated by BRENDA team
Treimer, J.F.; Zenk, M.H.
Strictosidine synthase from cell cultrues of Apocynaceae plants
FEBS Lett.
97
159-162
1979
Amsonia orientalis, Amsonia salicifolia, Catharanthus roseus, Ochrosia elliptica, Rauvolfia vomitoria, Stemmadenia tomentosa var. palmeri, Vinca major, Vinca minor, Voacanga africana
-
Manually annotated by BRENDA team
Pfitzner, U.; Zenk, M.H.
Immobilization of strictosidine synthase from Catharanthus cell cultures and preparative synthesis of strictosidine
Planta Med.
46
10-14
1982
Catharanthus roseus
Manually annotated by BRENDA team
Pfitzner, U.; Zenk, M.H.
Isoation and immobilization of strictosidine synthase
Methods Enzymol.
136
342-350
1987
Catharanthus roseus
-
Manually annotated by BRENDA team
Pennings, E.J.M.; Van den Bosch, R.A.; Van der Heijden, R.; Stevens, L.H.; Duine, J.A.; Verpoorte, R.
Assay of trictosidine synthase from plant cell cultures by high-performance liquid chromatography
Anal. Biochem.
176
412-415
1989
Catharanthus roseus, Tabernaemontana orientalis
Manually annotated by BRENDA team
Roessner, C.A.; Devagupta, R.; Hasan, M.; Williams, H.J.; Scott, A.I.
Purification of an indole alkaloid biosynthetic enzyme, strictosidine synthase, from a recombinant strain of Escherichia coli
Protein Expr. Purif.
3
295-300
1992
Catharanthus roseus
Manually annotated by BRENDA team
Stevens, L.H.; Giroud, C.; Pennings, E.J.M.; Verpoorte, R.
Purification and characterization of strictosidine synthase from a suspension culture of Cinchona robusta
Phytochemistry
33
99-106
1993
Catharanthus roseus, Cinchona robusta
-
Manually annotated by BRENDA team
de Waal, A.; Meijer, A.H.; Verpoorte, R.
Strictosidine synthase from Catharanthus roseus: purification and characterization of multiple forms
Biochem. J.
306
571-580
1995
Catharanthus roseus
Manually annotated by BRENDA team
Hallard, D.; Van der Heijden, R.; Verpoorte, R.; Lopes Cardoso, M.I.; Pasquali, G.; Memelink, J.; Hoge, J.H.C.
Suspension cultured transgenic cells of Nicotiana tabacum expressing tryptophan decarboxylase and strictosidine synthase cDNAs from Catharanthus roseus produce strictosidine upon secologanin feeding.
Plant Cell Rep.
17
50-54
1997
Catharanthus roseus
Manually annotated by BRENDA team
Canel, C.; Lopes-Cardoso, M.I.; Whitmer, S.; van der Fits, L.; Pasquali, G.; van der Heijden, R.; Hoge, J.H.; Verpoorte, R.
Effects of over-expression of strictosidine synthase and tryptophan decarboxylase on alkaloid production by cell cultures of Catharanthus roseus
Planta
205
414-419
1998
Catharanthus roseus (P18417), Catharanthus roseus
Manually annotated by BRENDA team
Pasquali, G.; Erven, A.S.; Ouwerkerk, P.B.; Menke, F.L.; Memelink, J.
The promoter of the strictosidine synthase gene from periwinkle confers elicitor-inducible expression in transgenic tobacco and binds nuclear factors GT-1 and GBF
Plant Mol. Biol.
39
1299-1310
1999
Catharanthus roseus
Manually annotated by BRENDA team
Whitmer, S.; van der Heijden, R.; Verpoorte, R.
Effect of precursor feeding on alkaloid accumulation by a strictosidine synthase over-expressing transgenic cell line S1 of Catharanthus roseus
Plant Cell Tissue Organ Cult.
69
85-93
2002
Catharanthus roseus
-
Manually annotated by BRENDA team
Chen, S.; Galan, M.C.; Coltharp, C.; OConnor, S.E.
Redesign of a central enzyme in alkaloid biosynthesis
Chem. Biol.
13
1137-1141
2006
Catharanthus roseus
Manually annotated by BRENDA team
Bernhardt, P.; McCoy, E.; OConnor, S.E.
Rapid identification of enzyme variants for reengineered alkaloid biosynthesis in periwinkle
Chem. Biol.
14
888-897
2007
Catharanthus roseus
Manually annotated by BRENDA team
Maresh, J.J.; Giddings, L.A.; Friedrich, A.; Loris, E.A.; Panjikar, S.; Trout, B.L.; Stoeckigt, J.; Peters, B.; OConnor, S.E.
Strictosidine synthase: mechanism of a Pictet-Spengler catalyzing enzyme
J. Am. Chem. Soc.
130
710-723
2008
Catharanthus roseus, Rauvolfia serpentina (P68175)
Manually annotated by BRENDA team
Stoeckigt, J.; Barleben, L.; Panjikar, S.; Loris, E.A.
3D-Structure and function of strictosidine synthase - the key enzyme of monoterpenoid indole alkaloid biosynthesis
Plant Physiol. Biochem.
46
340-355
2008
Catharanthus roseus (P18417), Rauvolfia serpentina (P68175), Rauvolfia serpentina
Manually annotated by BRENDA team
Guirimand, G.; Courdavault, V.; Lanoue, A.; Mahroug, S.; Guihur, A.; Blanc, N.; Giglioli-Guivarch, N.; St-Pierre, B.; Burlat, V.
Strictosidine activation in Apocynaceae: Towards a nuclear time bomb?
BMC Plant Biol.
10
182
2010
Catharanthus roseus
Manually annotated by BRENDA team
Verma, P.; Sharma, A.; Khan, S.A.; Shanker, K.; Mathur, A.K.
Over-expression of Catharanthus roseus tryptophan decarboxylase and strictosidine synthase in rol gene integrated transgenic cell suspensions of Vinca minor
Protoplasma
252
373-381
2015
Catharanthus roseus (P18417), Catharanthus roseus
Manually annotated by BRENDA team
Pandey, S.S.; Singh, S.; Babu, C.S.; Shanker, K.; Srivastava, N.K.; Shukla, A.K.; Kalra, A.
Fungal endophytes of Catharanthus roseus enhance vindoline content by modulating structural and regulatory genes related to terpenoid indole alkaloid biosynthesis
Sci. Rep.
6
26583
2016
Catharanthus roseus (P18417), Catharanthus roseus
Manually annotated by BRENDA team
Cui, L.; Ni, X.; Ji, Q.; Teng, X.; Yang, Y.; Wu, C.; Zekria, D.; Zhang, D.; Kai, G.
Co-overexpression of geraniol-10-hydroxylase and strictosidine synthase improves anti-cancer drug camptothecin accumulation in Ophiorrhiza pumila
Sci. Rep.
5
8227
2015
Catharanthus roseus (P18417), Catharanthus roseus
Manually annotated by BRENDA team
Sharma, A.; Verma, P.; Mathur, A.; Mathur, A.K.
Overexpression of tryptophan decarboxylase and strictosidine synthase enhanced terpenoid indole alkaloid pathway activity and antineoplastic vinblastine biosynthesis in Catharanthus roseus
Protoplasma
255
1281-1294
2018
Catharanthus roseus (P18417), Catharanthus roseus
Manually annotated by BRENDA team
Soltani, N.; Nazarian-Firouzabadi, F.; Shafeinia, A.; Sadr, A.S.; Shirali, M.
The expression of terpenoid indole alkaloid (TIAs) pathway genes in Catharanthus roseus in response to salicylic acid treatment
Mol. Biol. Rep.
47
7009-7016
2020
Catharanthus roseus (P18417), Catharanthus roseus
Manually annotated by BRENDA team