Information on EC 2.3.1.93 - 13-hydroxylupanine O-tigloyltransferase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.3.1.93
-
RECOMMENDED NAME
GeneOntology No.
13-hydroxylupanine O-tigloyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(E)-2-methylcrotonoyl-CoA + 13-hydroxylupanine = CoA + 13-[(E)-2-methylcrotonoyl]oxylupanine
show the reaction diagram
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-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acyl group transfer
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-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
lupanine biosynthesis
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-
Tropane, piperidine and pyridine alkaloid biosynthesis
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-
SYSTEMATIC NAME
IUBMB Comments
(E)-2-methylcrotonoyl-CoA:13-hydroxylupanine O-2-methylcrotonoyltransferase
Benzoyl-CoA and, more slowly, pentanoyl-CoA, 3-methylbutanoyl-CoA and butanoyl-CoA can act as acyl donors. Involved in the synthesis of lupanine alkaloids.
CAS REGISTRY NUMBER
COMMENTARY hide
85341-00-0
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
Lupinus hirsutus
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-
-
Manually annotated by BRENDA team
Lupinus polyphyllus x Lupinus arboreus
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-
-
Manually annotated by BRENDA team
no activity in Conium maculatum
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-
-
Manually annotated by BRENDA team
no activity in Cytisus scoparius
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-
-
Manually annotated by BRENDA team
no activity in Lupinus luteus
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-
-
Manually annotated by BRENDA team
no activity in Pisum sativum
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-
-
Manually annotated by BRENDA team
no activity in Vicia faba
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-
-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
3-methylbutyryl-CoA + 13-hydroxylupanine
CoA + 13-(3-methylbutyryl)oxylupanine
show the reaction diagram
-
97% of activity compared to tigloyl-CoA
-
ir
benzoyl-CoA + 13-alpha-hydroxymultiflorine
CoA + 13-benzoyloxymultiflorine
show the reaction diagram
-
-
-
?
benzoyl-CoA + 13-hydroxylupanine
CoA + 13-benzoyloxylupanine
show the reaction diagram
butyryl-CoA + 13-hydroxylupanine
CoA + 13-butyryloxylupanine
show the reaction diagram
-
27% of activity compared to tigloyl-CoA
-
ir
propionyl-CoA + 13-hydroxylupanine
CoA + 13-propionyloxylupanine
show the reaction diagram
-
25% of activity compared to tigloyl-CoA
-
ir
tigloyl-CoA + 13-alpha-hydroxymultiflorine
CoA + 13-tigloyloxymultiflorine
show the reaction diagram
tigloyl-CoA + 13-hydroxylupanine
CoA + 13-tigloyloxylupanine
show the reaction diagram
valeryl-CoA + 13-hydroxylupanine
CoA + 13-valeryloxylupanine
show the reaction diagram
-
73% of activity compared to tigloyl-CoA
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ir
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
tigloyl-CoA + 13-alpha-hydroxymultiflorine
CoA + 13-tigloyloxymultiflorine
show the reaction diagram
tigloyl-CoA + 13-hydroxylupanine
CoA + 13-tigloyloxylupanine
show the reaction diagram
additional information
?
-
Q5H873
control of quinolizidine alkaloid patterns in a tissue-specific manner
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-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
cations, e.g. Fe2+, Ca2+, Mg2+, NH4Cl, Fe3+ have no significant influence
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-epilupinine
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-
(+)-lupanine
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CoA
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competitive
diethyldithiocarbamate
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HgCl2
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strong
iodoacetamide
-
slight inhibition
N-ethylmaleimide
p-Chloromercuriphenyl sulfonic acid
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-
p-hydroxymercuribenzoate
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strong
additional information
-
EDTA is no inhibitor
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
dithiothreitol
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.021
13-alpha-hydroxymultiflorine
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-
0.018 - 0.027
13-hydroxylupanine
0.14 - 0.52
tigloyl-CoA
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3.1
(+)-epilupinine
-
-
1.7
(+)-lupanine
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-
0.5
CoA
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-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.12
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isoform A
2.18
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isoform B
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 8
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-
additional information
-
isoform 1 pI: 7.8, isoform 2 pI: 7.6
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5 - 8
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half-maximal activity at pH 6.5, maximal activity at pH 8.0
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
leaflet
Manually annotated by BRENDA team
additional information
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
50000
-
isoform A and B, gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
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1 * 50000, isoform A and B, SDS-PAGE
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
70
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5 min, complete inactivation
OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
O2-sensitive, dithioerythritol stabilizes
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487720
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
fusion protein with fused to glutathione S-transferase
partial
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli as a recombinant protein fused to glutathione S-transferase