HOME
login
history
all enzymes
BRENDA home
History
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
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
The expected taxonomic range for this enzyme is: Rauvolfia serpentina
topPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
EC NUMBER 
COMMENTARY 
2.3.1.160
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
RECOMMENDED NAME
GeneOntology No.
vinorine synthase
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
cyclization
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
CAS REGISTRY NUMBER
COMMENTARY
88844-97-7
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Rauvolfia serpentina x Rhazya stricta
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
35
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
Rauvolfia serpentina x Rhazya stricta
-
hybrid of Rauvolfia serpentina and Rhazya stricta
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PDB
SCOP
CATH
ORGANISM
UNIPROT
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
monomer
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
LINKS TO OTHER DATABASES (specific for EC-Number 2.3.1.160)
html completed
Use of this online version of BRENDA is free but requires a license. See terms of use.
Information
