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Information on EC 2.3.1.93 - 13-hydroxylupanine O-tigloyltransferase
for references in articles please use BRENDA:EC2.3.1.93
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EC Tree 2 Transferases
2.3 Acyltransferases
2.3.1 Transferring groups other than aminoacyl groups
2.3.1.93 13-hydroxylupanine O-tigloyltransferase
IUBMB Comments
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.
The enzyme appears in viruses and cellular organisms
Reaction Schemes
showSynonyms
13-hydroxylupanine o-tigloyltransferase, tigloyl-coa:(-)-13alpha-hydroxymultiflorine/(+)-13alpha-hydroxylupanine o-tigloyltransferase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
13-hydroxylupanine acyltransferase
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13-hydroxylupanine O-tigloyltransferase
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tigloyl-CoA:(-)-13alpha-hydroxymultiflorine/(+)-13alpha-hydroxylupanine O-tigloyltransferase
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tigloyl-CoA:13-hydroxylupanine O-tigloyltransferase
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tigloyltransferase, 13-hydroxylupanine
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(E)-2-methylcrotonoyl-CoA + 13-hydroxylupanine = CoA + 13-[(E)-2-methylcrotonoyl]oxylupanine
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Acyl group transfer
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PATHWAY SOURCE
PATHWAYS
MetaCyc
lupanine 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.
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CAS REGISTRY NUMBER
COMMENTARY
85341-00-0
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
3-methylbutyryl-CoA + 13-hydroxylupanine
CoA + 13-(3-methylbutyryl)oxylupanine
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Substrates: 97% of activity compared to tigloyl-CoA
Products: -
Products: -
ir
benzoyl-CoA + 13-alpha-hydroxymultiflorine
CoA + 13-benzoyloxymultiflorine
Substrates: -
Products: -
Products: -
?
butyryl-CoA + 13-hydroxylupanine
CoA + 13-butyryloxylupanine
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Substrates: 27% of activity compared to tigloyl-CoA
Products: -
Products: -
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propionyl-CoA + 13-hydroxylupanine
CoA + 13-propionyloxylupanine
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Substrates: 25% of activity compared to tigloyl-CoA
Products: -
Products: -
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valeryl-CoA + 13-hydroxylupanine
CoA + 13-valeryloxylupanine
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Substrates: 73% of activity compared to tigloyl-CoA
Products: -
Products: -
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benzoyl-CoA + 13-hydroxylupanine
CoA + 13-benzoyloxylupanine
Substrates: -
Products: -
Products: -
?
benzoyl-CoA + 13-hydroxylupanine
CoA + 13-benzoyloxylupanine
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Substrates: 111% of activity compared to tigloyl-CoA
Products: -
Products: -
ir
tigloyl-CoA + 13-alpha-hydroxymultiflorine
CoA + 13-tigloyloxymultiflorine
Substrates: -
Products: -
Products: -
?
tigloyl-CoA + 13-alpha-hydroxymultiflorine
CoA + 13-tigloyloxymultiflorine
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Substrates: tigloyl-CoA is (E)-2-methylcrotonoyl-CoA
Products: -
Products: -
?
tigloyl-CoA + 13-alpha-hydroxymultiflorine
CoA + 13-tigloyloxymultiflorine
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Substrates: isoform A and B
Products: -
Products: -
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tigloyl-CoA + 13-alpha-hydroxymultiflorine
CoA + 13-tigloyloxymultiflorine
Lupinus hirsutus
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Substrates: tigloyl-CoA is (E)-2-methylcrotonoyl-CoA
Products: -
Products: -
?
tigloyl-CoA + 13-hydroxylupanine
CoA + 13-tigloyloxylupanine
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Substrates: tigloyl-CoA is (E)-2-methylcrotonoyl-CoA
Products: -
Products: -
?
tigloyl-CoA + 13-hydroxylupanine
CoA + 13-tigloyloxylupanine
Substrates: -
Products: -
Products: -
?
tigloyl-CoA + 13-hydroxylupanine
CoA + 13-tigloyloxylupanine
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Substrates: tigloyl-CoA is (E)-2-methylcrotonoyl-CoA
Products: -
Products: -
?
tigloyl-CoA + 13-hydroxylupanine
CoA + 13-tigloyloxylupanine
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Substrates: tigloyl-CoA is (E)-2-methylcrotonoyl-CoA
Products: -
Products: -
ir
tigloyl-CoA + 13-hydroxylupanine
CoA + 13-tigloyloxylupanine
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Substrates: isoform A and B
Products: -
Products: -
?
tigloyl-CoA + 13-hydroxylupanine
CoA + 13-tigloyloxylupanine
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Substrates: enzyme is involved in the biosynthesis of quinolizidine alkaloid esters
Products: -
Products: -
?
tigloyl-CoA + 13-hydroxylupanine
CoA + 13-tigloyloxylupanine
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Substrates: tigloyl-CoA is (E)-2-methylcrotonoyl-CoA
Products: -
Products: -
?
tigloyl-CoA + 13-hydroxylupanine
CoA + 13-tigloyloxylupanine
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Substrates: enzyme is involved in the biosynthesis of quinolizidine alkaloid esters
Products: -
Products: -
?
tigloyl-CoA + 13-hydroxylupanine
CoA + 13-tigloyloxylupanine
Lupinus polyphyllus x Lupinus arboreus
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Substrates: tigloyl-CoA is (E)-2-methylcrotonoyl-CoA
Products: -
Products: -
?
additional information
?
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Substrates: substrate specificity, overview
Products: -
Products: -
?
additional information
?
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Substrates: lupinine, 4-hydroxylupinine, and cholesterol and acetyl-CoA are no substrates
Products: -
Products: -
?
additional information
?
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Substrates: baptifoline, epilupinine and lupinine are no substrates
Products: -
Products: -
?
additional information
?
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Substrates: control of quinolizidine alkaloid patterns in a tissue-specific manner
Products: -
Products: -
?
additional information
?
-
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Substrates: control of quinolizidine alkaloid patterns in a tissue-specific manner
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
tigloyl-CoA + 13-alpha-hydroxymultiflorine
CoA + 13-tigloyloxymultiflorine
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Substrates: tigloyl-CoA is (E)-2-methylcrotonoyl-CoA
Products: -
Products: -
?
tigloyl-CoA + 13-alpha-hydroxymultiflorine
CoA + 13-tigloyloxymultiflorine
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Substrates: isoform A and B
Products: -
Products: -
?
tigloyl-CoA + 13-hydroxylupanine
CoA + 13-tigloyloxylupanine
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Substrates: tigloyl-CoA is (E)-2-methylcrotonoyl-CoA
Products: -
Products: -
?
tigloyl-CoA + 13-hydroxylupanine
CoA + 13-tigloyloxylupanine
-
Substrates: isoform A and B
Products: -
Products: -
?
tigloyl-CoA + 13-hydroxylupanine
CoA + 13-tigloyloxylupanine
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Substrates: enzyme is involved in the biosynthesis of quinolizidine alkaloid esters
Products: -
Products: -
?
tigloyl-CoA + 13-hydroxylupanine
CoA + 13-tigloyloxylupanine
-
Substrates: tigloyl-CoA is (E)-2-methylcrotonoyl-CoA
Products: -
Products: -
?
tigloyl-CoA + 13-hydroxylupanine
CoA + 13-tigloyloxylupanine
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Substrates: enzyme is involved in the biosynthesis of quinolizidine alkaloid esters
Products: -
Products: -
?
additional information
?
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Substrates: control of quinolizidine alkaloid patterns in a tissue-specific manner
Products: -
Products: -
?
additional information
?
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Substrates: control of quinolizidine alkaloid patterns in a tissue-specific manner
Products: -
Products: -
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
cations, e.g. Fe2+, Ca2+, Mg2+, NH4Cl, Fe3+ have no significant influence
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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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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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
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). HLTT_LUPAL
453
0
51181
Swiss-Prot
other Location (Reliability: 5)
A0A396HUS5_MEDTR
53
0
5884
TrEMBL
Secretory Pathway (Reliability: 4)
A0A396HEG5_MEDTR
222
0
25018
TrEMBL
other Location (Reliability: 5)
A0A396H7Y1_MEDTR
52
0
5783
TrEMBL
other Location (Reliability: 4)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli as a recombinant protein fused to glutathione S-transferase
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Wink, M.; Hartmann, T.
Enzymatic synthesis of quinolizidine alkaloid esters: a tigloyl-CoA:13-hydroxylupanine O-tigloyl transferase from Lupinus albus L.
Planta
156
560-565
1982
Lupinus albus, Lupinus polyphyllus, no activity in Conium maculatum, no activity in Cytisus scoparius, no activity in Pisum sativum, no activity in Vicia faba
brenda
Suzuki, H.; Murakoshi, I.; Saito, K.
A novel O-tigloyltransferase for alkaloid biosynthesis in plants. Purification, characterization, and distribution in Lupinus plants
J. Biol. Chem.
269
15853-15860
1994
Cytisus scoparius, Lupinus albus, Lupinus hirsutus, Lupinus polyphyllus x Lupinus arboreus, no activity in Lupinus luteus
brenda
Okada, T.; Hirai, M.Y.; Suzuki, H.; Yamazaki, M.; Saito, K.
Molecular characterization of a novel quinolizidine alkaloid O-tigloyltransferase: cDNA cloning, catalytic activity of recombinant protein and expression analysis in Lupinus plants
Plant Cell Physiol.
46
233-244
2005
Lupinus albus (Q5H873), Lupinus albus
brenda
EXTERNAL LINKS (specific for EC-Number 2.3.1.93)
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Release 2023.1 (January 2023)
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