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EC Tree
IUBMB Comments 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.
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
vinorine synthase,
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vinorine synthase
-
a member of the BAHD enzyme super-family, benzylalcohol acetyl-, anthocyanin-O-hydroxy-cinnamoyl-, anthranilate-N-hydroxy-cinnamoyl-benzoyl- and deacetylvindoline acetyl transferase, involved in synthesis of ajmaline
vinorine synthase
Rauvolfia serpentina x Rhazya stricta
-
-
vinorine synthase
Rauvolfia serpentina x Rhazya stricta
-
VS
-
-
VS
Rauvolfia serpentina x Rhazya stricta
-
-
VS
Rauvolfia serpentina x Rhazya stricta
-
additional information
enzyme belongs to the BAHD enzyme super family
additional information
Rauvolfia serpentina x Rhazya stricta
-
enzyme probably belongs to the BAHD enzyme super family
additional information
Rauvolfia serpentina x Rhazya stricta
enzyme belongs to the BAHD acetyltransferase super family
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acetyl-CoA + 16-epivellosimine = CoA + vinorine
acetyl-CoA + 16-epivellosimine = CoA + vinorine
-
-
-
-
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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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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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
acetyl-CoA + gardneral
CoA + 11-methoxyvinorine
additional information
?
-
acetyl-CoA + 16-epivellosimine
CoA + vinorine
-
-
-
?
acetyl-CoA + 16-epivellosimine
CoA + vinorine
-
-
r
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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acetyl-CoA + 16-epivellosimine
CoA + vinorine
acetyl-CoA + 16-epivellosimine
CoA + vinorine
-
-
-
-
?
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
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4-(2-aminoethyl)-benzenesulfonyl fluoride
Rauvolfia serpentina x Rhazya stricta
selective Ser modifying reagent, complete inhibition
diethyldicarbonate
Rauvolfia serpentina x Rhazya stricta
complete inhibition
Hg2+
Rauvolfia serpentina x Rhazya stricta
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
PMSF
Rauvolfia serpentina x Rhazya stricta
58% inhibition
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0.039
11-methoxy-16-epivellosimine
-
-
0.0194
16-epivellosimine
-
-
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
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
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
0.027
gardneral
Rauvolfia serpentina x Rhazya stricta
pH 7.0, 30°C, recombinant mutant C89A
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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
0.085
gardneral
Rauvolfia serpentina x Rhazya stricta
pH 7.0, 30°C, recombinant mutant S413A
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99.1
Rauvolfia serpentina x Rhazya stricta
-
purified enzyme
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7
Rauvolfia serpentina x Rhazya stricta
-
assay at
7.8
Rauvolfia serpentina x Rhazya stricta
-
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30
Rauvolfia serpentina x Rhazya stricta
-
assay at
35
-
-
35
Rauvolfia serpentina x Rhazya stricta
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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5
Rauvolfia serpentina x Rhazya stricta
sequence calculation
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Rauvolfia serpentina x Rhazya stricta
-
-
-
brenda
-
Uniprot
brenda
-
-
-
brenda
Rauvolfia serpentina x Rhazya stricta
hybrid
-
-
brenda
Rauvolfia serpentina x Rhazya stricta
hybrid
SwissProt
brenda
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Rauvolfia serpentina x Rhazya stricta
-
hybrid of Rauvolfia serpentina and Rhazya stricta
brenda
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VINSY_RAUSE
421
0
46828
Swiss-Prot
other Location (Reliability: 2 )
A0A2P6PBR4_ROSCH
481
0
53984
TrEMBL
Mitochondrion (Reliability: 4 )
A0A2P6Q8X4_ROSCH
154
0
17308
TrEMBL
other Location (Reliability: 4 )
A0A396HBB8_MEDTR
92
0
10759
TrEMBL
other Location (Reliability: 2 )
G7J2I5_MEDTR
416
0
47429
TrEMBL
other Location (Reliability: 2 )
A0A2P6RFY1_ROSCH
271
0
30564
TrEMBL
other Location (Reliability: 2 )
A0A2P6PZH6_ROSCH
486
0
53449
TrEMBL
other Location (Reliability: 3 )
A0A2G9GZV5_9LAMI
244
1
28117
TrEMBL
other Location (Reliability: 2 )
A0A2P6QX43_ROSCH
306
0
34344
TrEMBL
other Location (Reliability: 2 )
A0A072U3X3_MEDTR
437
0
49975
TrEMBL
other Location (Reliability: 3 )
A0A2P6RFZ0_ROSCH
445
0
49980
TrEMBL
other Location (Reliability: 3 )
A0A2P6R0R8_ROSCH
447
0
50183
TrEMBL
other Location (Reliability: 3 )
A0A2G9H2H7_9LAMI
262
0
30263
TrEMBL
other Location (Reliability: 2 )
A0A2G9GH95_9LAMI
207
0
23567
TrEMBL
other Location (Reliability: 2 )
A0A2G9HBK3_9LAMI
429
0
48508
TrEMBL
other Location (Reliability: 2 )
A0A2G9FWN6_9LAMI
379
0
42898
TrEMBL
other Location (Reliability: 2 )
A0A2P6R0Z9_ROSCH
427
0
47888
TrEMBL
other Location (Reliability: 2 )
A0A2P6Q8Y4_ROSCH
445
0
49960
TrEMBL
other Location (Reliability: 1 )
A0A2G9G0L2_9LAMI
300
1
33770
TrEMBL
Secretory Pathway (Reliability: 3 )
A0A2G9HBK8_9LAMI
416
0
46966
TrEMBL
other Location (Reliability: 2 )
G7IL69_MEDTR
457
0
51514
TrEMBL
other Location (Reliability: 4 )
A0A2P6RDB0_ROSCH
466
0
51989
TrEMBL
other Location (Reliability: 2 )
A0A2P6PY35_ROSCH
257
0
29346
TrEMBL
other Location (Reliability: 4 )
A0A2P6R0U0_ROSCH
430
0
47773
TrEMBL
other Location (Reliability: 2 )
A0A2G9FYD5_9LAMI
434
0
48845
TrEMBL
other Location (Reliability: 4 )
A0A2P6PBR1_ROSCH
199
1
22172
TrEMBL
Mitochondrion (Reliability: 4 )
A0A2G9H0M0_9LAMI
424
0
47785
TrEMBL
other Location (Reliability: 2 )
A0A2G9H990_9LAMI
432
0
48351
TrEMBL
other Location (Reliability: 4 )
A0A2G9GRX3_9LAMI
348
0
39199
TrEMBL
other Location (Reliability: 5 )
A0A2P6SC52_ROSCH
208
0
22960
TrEMBL
other Location (Reliability: 3 )
A0A2P6Q9B9_ROSCH
444
0
49253
TrEMBL
other Location (Reliability: 2 )
A0A2P6Q8X1_ROSCH
435
0
48276
TrEMBL
other Location (Reliability: 2 )
A0A2G9G7H4_9LAMI
416
0
46956
TrEMBL
other Location (Reliability: 1 )
A0A2G9HC63_9LAMI
331
0
37357
TrEMBL
other Location (Reliability: 4 )
A0A2G9FYU1_9LAMI
408
0
45460
TrEMBL
other Location (Reliability: 3 )
A0A072TSP7_MEDTR
453
0
51527
TrEMBL
other Location (Reliability: 2 )
A0A2P6R0S8_ROSCH
445
0
50005
TrEMBL
other Location (Reliability: 3 )
A0A2P6QX71_ROSCH
425
0
47961
TrEMBL
other Location (Reliability: 2 )
I4G0C0_MICAE
447
0
51811
TrEMBL
-
A0A2G9HBJ0_9LAMI
221
0
25167
TrEMBL
other Location (Reliability: 1 )
G7K7H1_MEDTR
439
0
50438
TrEMBL
other Location (Reliability: 4 )
A0A2P6R0T6_ROSCH
447
0
50315
TrEMBL
other Location (Reliability: 2 )
A0A2P6P5P4_ROSCH
442
0
50429
TrEMBL
other Location (Reliability: 2 )
A0A2G9GDF5_9LAMI
155
0
17917
TrEMBL
Chloroplast (Reliability: 5 )
G7K7H3_MEDTR
440
0
50972
TrEMBL
other Location (Reliability: 3 )
A0A2G9HJQ5_9LAMI
429
0
48102
TrEMBL
other Location (Reliability: 2 )
A0A072TTM6_MEDTR
436
0
49408
TrEMBL
other Location (Reliability: 3 )
A0A2P6Q999_ROSCH
443
0
50082
TrEMBL
other Location (Reliability: 2 )
A0A2P6R0T4_ROSCH
439
0
49995
TrEMBL
other Location (Reliability: 2 )
A0A2P6R0S6_ROSCH
263
0
29061
TrEMBL
Secretory Pathway (Reliability: 2 )
A0A2G9G7U4_9LAMI
415
0
46680
TrEMBL
other Location (Reliability: 1 )
A0A2G9HBJ2_9LAMI
427
0
48078
TrEMBL
other Location (Reliability: 2 )
A0A2P6R0V9_ROSCH
430
0
48363
TrEMBL
other Location (Reliability: 2 )
A0A2G9HEC5_9LAMI
440
0
49522
TrEMBL
other Location (Reliability: 2 )
A0A2G9I9G5_9LAMI
414
0
46556
TrEMBL
Secretory Pathway (Reliability: 5 )
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.
42000
Rauvolfia serpentina x Rhazya stricta
-
about, gel filtration
46800
Rauvolfia serpentina x Rhazya stricta
1 x * 46800, wild-type untagged enzyme
50000
Rauvolfia serpentina x Rhazya stricta
-
1 * 50000, about, SDS-PAGE
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monomer
two-domain structure
monomer
Rauvolfia serpentina x Rhazya stricta
-
1 * 50000, about, SDS-PAGE
monomer
Rauvolfia serpentina x Rhazya stricta
1 x * 46800, wild-type untagged enzyme
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
using the hanging-drop vapour-diffusion method
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
D164A
-
reduction in enzyme activity
D32A
-
reduction in enzyme activity
D362A
-
reduction in enzyme activity
H160A
-
reduction in enzyme activity
S29A
-
reduction in enzyme activity
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
S68A
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.
991fold from cell suspension culture by anion exchange, hydrophobic interaction, and hydroxyapatite chromatography, and gel filtration
Rauvolfia serpentina x Rhazya stricta
-
of the recombinant protein by his-tag affinity column chromatography
-
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.
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
expression in Escherichia coli
-
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.
Pfitzner, A.; Polz, L.; Stöckligt, J.
Properties of vinorine synthase the Rauwolfia enzyme involved in the formation of the ajmaline skeleton
Z. Naturforsch. C
41
103-114
1986
Rauvolfia serpentina
-
brenda
Pfitzner, A.; Stoeckigt, J.
Biogenetic link between sarpagine and ajmaline type alkaloids
Tetrahedron Lett.
24
5197-5200
1983
Rauvolfia serpentina
-
brenda
Gerasimenko, I.; Ma, X.; Sheludko, Y.; Mentele, R.; Lottspeich, F.; Stockigt, J.
Purification and partial amino acid sequences of the enzyme vinorine synthase involved in a crucial step of ajmaline biosynthesis
Bioorg. Med. Chem.
12
2781-2786
2004
Rauvolfia serpentina x Rhazya stricta
brenda
Bayer, A.; Ma, X.; Stockigt, J.
Acetyltransfer in natural product biosynthesis - functional cloning and molecular analysis of vinorine synthase
Bioorg. Med. Chem.
12
2787-2795
2004
Rauvolfia serpentina x Rhazya stricta (Q70PR7)
brenda
Ma, X.; Koepke, J.; Panjikar, S.; Fritzsch, G.; Stockigt, J.
Crystal structure of vinorine synthase, the first representative of the BAHD superfamily
J. Biol. Chem.
280
13576-13583
2005
Rauvolfia serpentina (Q70PR7)
brenda
Stoeckigt, J.; Panjikar, S.; Ruppert, M.; Barleben, L.; Ma, X.; Loris, E.; Hill, M.
The molecular architecture of major enzymes from ajmaline biosynthetic pathway
Phytochem. Rev.
6
15-34
2007
Rauvolfia serpentina
-
brenda
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2.3.1.160 vinorine synthase
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