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Enzyme Nomenclature
Information on EC 2.3.1.160 - vinorine synthase
for references in articles please use BRENDA:EC2.3.1.160
Word Map on EC 2.3.1.160
- 2.3.1.160
- rauvolfia
- ajmaline
-
acyltransferases
- serpentina
-
antiarrhythmic
-
alkaloid
-
monoterpenoid
- indole
- vindoline
-
coa-dependent
- gardneral
- morphine
-
hanging-drop
- deacetylvindoline
- peg
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The expected taxonomic range for this enzyme is: Rauvolfia serpentina
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EC NUMBER 
COMMENTARY 
2.3.1.160
-
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RECOMMENDED NAME
GeneOntology No.
vinorine synthase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
acetyl-CoA + 16-epivellosimine = CoA + vinorine
; The reaction proceeds in two stages. The indole nitrogen of 16-epivellosimine interacts with its aldehyde group giving an hydroxy-substituted new ring. This alcohol is then acetylated. Also acts on gardneral, 11-methoxy-16-epivellosimine. Generates the ajmalan skeleton, which forms part of the route to ajmaline
-
-
-
acetyl-CoA + 16-epivellosimine = CoA + vinorine
His160 and Asp164 are catalytic site residues of the non-triad motif HxxxD
Rauvolfia serpentina x Rhazya stricta
acetyl-CoA + 16-epivellosimine = CoA + vinorine
His160 of the HxxxD motif functions as a general base in catalysis, located at the center of the reaction channel at the interface of both domains and is accessible from both sides
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
cyclization
-
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
acyl-CoA:16-epivellosimine O-acetyltransferase (cyclizing)
The reaction proceeds in two stages. The indole nitrogen of 16-epivellosimine interacts with its aldehyde group giving an hydroxy-substituted new ring. This alcohol is then acetylated. Also acts on gardneral (11-methoxy-16-epivellosimine). Generates the ajmalan skeleton, which forms part of the route to ajmaline.
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CAS REGISTRY NUMBER
COMMENTARY
88844-97-7
-
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Rauvolfia serpentina x Rhazya stricta
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
11-methoxy-16-epivellosimine + acetyl-CoA
CoA + 11-methoxy-vinorine
-
-
-
-
?
16-epi-vellosimine + acetyl-CoA
vinorine + CoA
-
VS responsible for generation of the basic carbon skeleton of the target compound ajmaline, His160 and Asp164 are the most important amino acids for the catalytic process, His-X-X-X-Asp sequence together with Asp-Phe-Gly-Trp-Gly are highly conserved motifs in acyltransferases
-
-
?
acetyl-CoA + 16-epivellosimine
CoA + vinorine
the enzyme is involved in a crucial step of antiarrhythmic drug ajmaline biosynthesis, pathway overview
-
-
r
acetyl-CoA + 16-epivellosimine
CoA + vinorine
Rauvolfia serpentina x Rhazya stricta
-
the enzyme is involved in a crucial step of antiarrhythmic drug ajmaline biosynthesis, pathway overview
-
-
?
acetyl-CoA + 16-epivellosimine
CoA + vinorine
Rauvolfia serpentina x Rhazya stricta
the enzyme is involved in a crucial step of antiarrhythmic drug ajmaline biosynthesis, pathway overview
-
-
r
acetyl-CoA + 16-epivellosimine
CoA + vinorine
Rauvolfia serpentina x Rhazya stricta
substrate specificity in both reaction directions, the reverse reaction is preferred
-
-
r
acetyl-CoA + 16-epivellosimine
CoA + vinorine
Rauvolfia serpentina x Rhazya stricta
-
the forward reaction is preferred
-
-
r
acetyl-CoA + gardneral
CoA + 11-methoxyvinorine
Rauvolfia serpentina x Rhazya stricta
i.e. 11-methoxy-16-epivellosimine, sarpagan-type alkaloid
ajmalin-type alkaloid
-
r
acetyl-CoA + gardneral
CoA + 11-methoxyvinorine
Rauvolfia serpentina x Rhazya stricta
-
sarpagan-type alkaloid, the forward reaction is preferred
ajmalin-type alkaloid
-
r
additional information
?
-
Rauvolfia serpentina x Rhazya stricta
no activity with polyneuridine, vomilenine, 17-O-acetyl-norajmaline, and N-methylgardneral
-
-
-
additional information
?
-
Rauvolfia serpentina x Rhazya stricta
-
the acetylation is important for stabilization of the immediate indolenine 17-deacetyl-vinorine, which would otherwise be spontaneously re-transformed
-
-
-
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
acetyl-CoA + 16-epivellosimine
CoA + vinorine
Q70PR7
the enzyme is involved in a crucial step of antiarrhythmic drug ajmaline biosynthesis, pathway overview
-
-
r
acetyl-CoA + 16-epivellosimine
CoA + vinorine
Rauvolfia serpentina x Rhazya stricta
-
the enzyme is involved in a crucial step of antiarrhythmic drug ajmaline biosynthesis, pathway overview
-
-
?
acetyl-CoA + 16-epivellosimine
CoA + vinorine
Rauvolfia serpentina x Rhazya stricta
Q70PR7
the enzyme is involved in a crucial step of antiarrhythmic drug ajmaline biosynthesis, pathway overview
-
-
r
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
4-(2-aminoethyl)-benzenesulfonyl fluoride
Rauvolfia serpentina x Rhazya stricta
selective Ser modifying reagent, complete inhibition
N-(N-(L-3-trans-carboxirane-2-carbonyl)-L-leucyl)-agmantine
Rauvolfia serpentina x Rhazya stricta
i.e. E64, selective Cys modifying reagent, 50% inhibition
-
N-tosyl-L-phenylalanine chloromethylketone
Rauvolfia serpentina x Rhazya stricta
complete inhibition
Nalpha-p-tosyl-L-lysine chloromethylketone
Rauvolfia serpentina x Rhazya stricta
50% inhibition
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.063
CoA
Rauvolfia serpentina x Rhazya stricta
pH 7.0, 30°C, recombinant wild-type enzyme
0.01
vinorine
Rauvolfia serpentina x Rhazya stricta
pH 7.0, 30°C, recombinant wild-type enzyme
0.057
acetyl-CoA
Rauvolfia serpentina x Rhazya stricta
pH 7.0, 30°C, recombinant wild-type enzyme
0.0011
gardneral
Rauvolfia serpentina x Rhazya stricta
pH 7.0, 30°C, recombinant mutant C149A
0.0026
gardneral
Rauvolfia serpentina x Rhazya stricta
pH 7.0, 30°C, recombinant mutant N293A
0.0047
gardneral
Rauvolfia serpentina x Rhazya stricta
pH 7.0, 30°C, recombinant mutant S29A
0.0075
gardneral
Rauvolfia serpentina x Rhazya stricta
pH 7.0, 30°C, recombinant wild-type enzyme
0.021
gardneral
Rauvolfia serpentina x Rhazya stricta
pH 7.0, 30°C, recombinant mutant S413A
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.735
vinorine
Rauvolfia serpentina x Rhazya stricta
pH 7.0, 30°C, recombinant wild-type enzyme
0.008
gardneral
Rauvolfia serpentina x Rhazya stricta
pH 7.0, 30°C, recombinant mutant C149A
0.018
gardneral
Rauvolfia serpentina x Rhazya stricta
pH 7.0, 30°C, recombinant mutant S29A
0.043
gardneral
Rauvolfia serpentina x Rhazya stricta
pH 7.0, 30°C, recombinant mutant N293A
0.065 - 0.103
gardneral
Rauvolfia serpentina x Rhazya stricta
pH 7.0, 30°C, recombinant wild-type enzyme
0.068
gardneral
Rauvolfia serpentina x Rhazya stricta
pH 7.0, 30°C, recombinant mutant C89A
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
35
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
Rauvolfia serpentina x Rhazya stricta
-
hybrid of Rauvolfia serpentina and Rhazya stricta
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
monomer
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Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
purified detagged recombinant wild-type or selenomethionine-labeled enzyme, hanging drop vapour diffusion method, 32°C, 2-3 mg/ml protein in 20 mM Tris-HCl, pH 7.5, 10 mM 2-mercaptoethanol, 1 mM EDTA, 0.5 mM acetyl-CoA, with reservoir solution containing 0.1 M Tris-HCl, pH 8.7, 2 M ammonium sulfate, 2% PEG 400, cryoprotection by 20-25% glycerol, X-ray diffraction structure determination anad analysis at 2.6 A resolution, modeling of CoA binding
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
991fold from cell suspension culture by anion exchange, hydrophobic interaction, and hydroxyapatite chromatography, and gel filtration
Rauvolfia serpentina x Rhazya stricta
-
recombinant N-terminally His-tagged wild-type and mutant enzymes from Escherichia coli to homogeneity
Rauvolfia serpentina x Rhazya stricta
recombinant soluble N-terminally His-tagged enzyme from Escherichia coli by nickel affinity chromatography and gel filtration
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA sequence determination and analysis, functional overexpression of N-terminally His-tagged wild-type and mutant enzymes in Escherichia coli
Rauvolfia serpentina x Rhazya stricta
overexpression of N-terminally His-tagged enzyme in Escherichia coli
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
C149A
Rauvolfia serpentina x Rhazya stricta
site-directed mutagenesis, 10% of wild-type activity
C89A
Rauvolfia serpentina x Rhazya stricta
site-directed mutagenesis, activity similar to the wild-type enzyme
D164A
Rauvolfia serpentina x Rhazya stricta
site-directed mutagenesis, inactive mutant
D32A
Rauvolfia serpentina x Rhazya stricta
site-directed mutagenesis, 14% of wild-type activity
D360A
Rauvolfia serpentina x Rhazya stricta
site-directed mutagenesis, activity similar to the wild-type enzyme
D362A
Rauvolfia serpentina x Rhazya stricta
site-directed mutagenesis, 35% of wild-type activity
H160A
Rauvolfia serpentina x Rhazya stricta
site-directed mutagenesis, inactive mutant
N293A
Rauvolfia serpentina x Rhazya stricta
site-directed mutagenesis, 68% of wild-type activity
S16A
Rauvolfia serpentina x Rhazya stricta
site-directed mutagenesis, 71% of wild-type activity
S243A
Rauvolfia serpentina x Rhazya stricta
site-directed mutagenesis, 17% of wild-type activity
S29A
Rauvolfia serpentina x Rhazya stricta
site-directed mutagenesis, 25% of wild-type activity
S413A
Rauvolfia serpentina x Rhazya stricta
site-directed mutagenesis, activity similar to the wild-type enzyme
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LINKS TO OTHER DATABASES (specific for EC-Number 2.3.1.160)
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