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Information on EC 2.3.1.160 - vinorine synthase
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EC Tree
2.3.1.160 vinorine synthaseIUBMB 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.
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Word Map
- 2.3.1.160
- rauvolfia
- ajmaline
- acyltransferases
- serpentina
-
antiarrhythmic
- indole
-
monoterpenoid
- morphine
- gardneral
-
hanging-drop
-
coa-dependent
-
hxxxd
- vindoline
- strictosidine
- deacetylvindoline
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
vinorine synthase, 
more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
vinorine synthase
VS
additional information
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
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
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
cyclization
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
-
-
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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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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 SUBSTRATE
NATURAL 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
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
-
-
?
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INHIBITOR
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)-agmatine
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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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Rauvolfia serpentina x Rhazya stricta
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
Rauvolfia serpentina x Rhazya stricta
-
hybrid of Rauvolfia serpentina and Rhazya stricta
brenda
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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). VINSY_RAUSE
421
0
46828
Swiss-Prot
other Location (Reliability: 2)
G7J2I5_MEDTR
416
0
47429
TrEMBL
other Location (Reliability: 2)
A0A072U3X3_MEDTR
437
0
49975
TrEMBL
other Location (Reliability: 3)
A0A2G9HJQ5_9LAMI
429
0
48102
TrEMBL
other Location (Reliability: 2)
A0A2P6RFY1_ROSCH
271
0
30564
TrEMBL
other Location (Reliability: 2)
A0A2G9HBJ0_9LAMI
221
0
25167
TrEMBL
other Location (Reliability: 1)
A0A2G9GH95_9LAMI
207
0
23567
TrEMBL
other Location (Reliability: 2)
A0A2G9FYU1_9LAMI
408
0
45460
TrEMBL
other Location (Reliability: 3)
A0A072TSP7_MEDTR
453
0
51527
TrEMBL
other Location (Reliability: 2)
G7K7H1_MEDTR
439
0
50438
TrEMBL
other Location (Reliability: 4)
A0A2G9H990_9LAMI
432
0
48351
TrEMBL
other Location (Reliability: 4)
A0A2G9H2H7_9LAMI
262
0
30263
TrEMBL
other Location (Reliability: 2)
A0A2G9I9G5_9LAMI
414
0
46556
TrEMBL
Secretory Pathway (Reliability: 5)
A0A2P6Q9B9_ROSCH
444
0
49253
TrEMBL
other Location (Reliability: 2)
A0A2P6Q8X4_ROSCH
154
0
17308
TrEMBL
other Location (Reliability: 4)
A0A2P6PBR1_ROSCH
199
1
22172
TrEMBL
Mitochondrion (Reliability: 4)
A0A2G9G7H4_9LAMI
416
0
46956
TrEMBL
other Location (Reliability: 1)
A0A2P6R0S8_ROSCH
445
0
50005
TrEMBL
other Location (Reliability: 3)
A0A2G9FWN6_9LAMI
379
0
42898
TrEMBL
other Location (Reliability: 2)
G7K7H3_MEDTR
440
0
50972
TrEMBL
other Location (Reliability: 3)
A0A2G9GZV5_9LAMI
244
1
28117
TrEMBL
other Location (Reliability: 2)
A0A2P6PZH6_ROSCH
486
0
53449
TrEMBL
other Location (Reliability: 3)
A0A2P6R0U0_ROSCH
430
0
47773
TrEMBL
other Location (Reliability: 2)
A0A2P6Q8Y4_ROSCH
445
0
49960
TrEMBL
other Location (Reliability: 1)
A0A2P6R0V9_ROSCH
430
0
48363
TrEMBL
other Location (Reliability: 2)
A0A2G9G7U4_9LAMI
415
0
46680
TrEMBL
other Location (Reliability: 1)
A0A2P6PBR4_ROSCH
481
0
53984
TrEMBL
Mitochondrion (Reliability: 4)
A0A2P6SC52_ROSCH
208
0
22960
TrEMBL
other Location (Reliability: 3)
A0A2P6RFZ0_ROSCH
445
0
49980
TrEMBL
other Location (Reliability: 3)
A0A2P6P5P4_ROSCH
442
0
50429
TrEMBL
other Location (Reliability: 2)
A0A2G9GRX3_9LAMI
348
0
39199
TrEMBL
other Location (Reliability: 5)
A0A2P6R0T6_ROSCH
447
0
50315
TrEMBL
other Location (Reliability: 2)
A0A2G9HBJ2_9LAMI
427
0
48078
TrEMBL
other Location (Reliability: 2)
A0A2G9FYD5_9LAMI
434
0
48845
TrEMBL
other Location (Reliability: 4)
A0A2P6QX43_ROSCH
306
0
34344
TrEMBL
other Location (Reliability: 2)
A0A2P6R0Z9_ROSCH
427
0
47888
TrEMBL
other Location (Reliability: 2)
A0A2G9HEC5_9LAMI
440
0
49522
TrEMBL
other Location (Reliability: 2)
A0A2G9H0M0_9LAMI
424
0
47785
TrEMBL
other Location (Reliability: 2)
A0A072TTM6_MEDTR
436
0
49408
TrEMBL
other Location (Reliability: 3)
A0A2P6R0S6_ROSCH
263
0
29061
TrEMBL
Secretory Pathway (Reliability: 2)
A0A2P6PY35_ROSCH
257
0
29346
TrEMBL
other Location (Reliability: 4)
A0A396HBB8_MEDTR
92
0
10759
TrEMBL
other Location (Reliability: 2)
G7IL69_MEDTR
457
0
51514
TrEMBL
other Location (Reliability: 4)
A0A2P6R0T4_ROSCH
439
0
49995
TrEMBL
other Location (Reliability: 2)
A0A2P6Q8X1_ROSCH
435
0
48276
TrEMBL
other Location (Reliability: 2)
A0A2P6RDB0_ROSCH
466
0
51989
TrEMBL
other Location (Reliability: 2)
A0A2P6QX71_ROSCH
425
0
47961
TrEMBL
other Location (Reliability: 2)
A0A2G9GDF5_9LAMI
155
0
17917
TrEMBL
Chloroplast (Reliability: 5)
A0A2G9HBK3_9LAMI
429
0
48508
TrEMBL
other Location (Reliability: 2)
A0A2G9G0L2_9LAMI
300
1
33770
TrEMBL
Secretory Pathway (Reliability: 3)
A0A2G9HBK8_9LAMI
416
0
46966
TrEMBL
other Location (Reliability: 2)
A0A2P6R0R8_ROSCH
447
0
50183
TrEMBL
other Location (Reliability: 3)
A0A2P6Q999_ROSCH
443
0
50082
TrEMBL
other Location (Reliability: 2)
A0A2G9HC63_9LAMI
331
0
37357
TrEMBL
other Location (Reliability: 4)
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
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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PROTEIN VARIANTS
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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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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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Pfitzner, A.; Polz, L.; Stckligt, 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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