Information on EC 2.1.1.50 - loganate O-methyltransferase

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)


The expected taxonomic range for this enzyme is: Catharanthus roseus

EC NUMBER
COMMENTARY hide
2.1.1.50
-
RECOMMENDED NAME
GeneOntology No.
loganate O-methyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + loganate = S-adenosyl-L-homocysteine + loganin
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
methyl group transfer
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
-
Monoterpenoid biosynthesis
-
-
secologanin and strictosidine biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:loganate 11-O-methyltransferase
Also acts on secologanate. Methylates the 11-carboxy group of the monoterpenoid loganate.
CAS REGISTRY NUMBER
COMMENTARY hide
39391-10-1
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
enzyme in the monoterpenoid indole alkaloid biosynthesis pathway
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
loganic acid + S-adenosyl-L-methionine
loganin + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
?
S-adenosyl-L-methionine + loganate
S-adenosyl-L-homocysteine + loganin
show the reaction diagram
S-adenosyl-L-methionine + secologanate
S-adenosyl-L-homocysteine + secologanin
show the reaction diagram
-
-
-
-
?
secologanic acid + S-adenosyl-L-methionine
secologanin + S-adenosyl-L-homocysteine
show the reaction diagram
10% activity compared to loganic acid
-
-
?
additional information
?
-
-
no significant methylation of: 7-deoxyloganic acid, geniposidic acid, 7-epiloganic acid
-
-
-
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
loganic acid + S-adenosyl-L-methionine
loganin + S-adenosyl-L-homocysteine
show the reaction diagram
B2KPR3
-
-
-
?
S-adenosyl-L-methionine + loganate
S-adenosyl-L-homocysteine + loganin
show the reaction diagram
-
biosynthesis of indole alkaloids
-
-
?
S-adenosyl-L-methionine + secologanate
S-adenosyl-L-homocysteine + secologanin
show the reaction diagram
-
-
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
Mg2+ or K+ are not required for enzyme activity nor to enhance it
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
dependency on divalent metal cations not detected
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
iodoacetamide
-
-
loganin
reaction product
N-Methylmaleimide
-
-
p-chloromercuribenzoate
-
-
S-adenosyl-L-homocysteine
-
S-adenosyl-L-methionine
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
12.5 - 14.76
loganic acid
742.1
S-adenosyl-L-methionine
pH 7.5, 37C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.327
loganic acid
Catharanthus roseus
B2KPR3
pH 7.5, 37C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.215
loganin
pH 7.5, 37C
0.4
S-adenosyl-L-homocysteine
pH 7.5, 37C
0.2
S-adenosyl-L-methionine
pH 7.5, 37C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.000000517
secologanic acid, buffer (100 mM Tris-HCl, pH 7.5, 14 mM beta-mercaptoethanol, 25 mM KCl), 37C, 30 min assay
0.00000517
loganic acid, buffer (100 mM Tris-HCl, pH 7.5, 14 mM beta-mercaptoethanol, 25 mM KCl), 37C, 30 min assay
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.2
-
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
32 - 33
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
highest activity
Manually annotated by BRENDA team
10fold higher enzyme activity in epidermis extracts than in whole leaves, 50% lower activity in aged L2, L3, and L4 leaves compared to young L1 leaves
Manually annotated by BRENDA team
4-8times lower activity than in the other tested plant organs
Manually annotated by BRENDA team
similar activity as in leaves
Manually annotated by BRENDA team
second highest activity
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
42020
calculated from 371-amino acid open reading frame
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
crude recombinant enzyme, for enzyme activity location study upper and lower epidermis of leaves is abraded with carborundum, leaves rubbed with cotton swabs and then dipped in Trizol at 4C and agitated
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
PCR-amplification of cDNA, insertion into expression vector pET 30b, ligated into pGEM-TEasy, heat shock transformation of Escherichia coli DE3-MRF
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pharmacology
Catharanthus roseus is the sole commercial source for monoterpenoid indole alkaloids vindoline and catharanthine, components of the anticancer dimers vinblastine and vincristine