Information on EC 2.1.1.101 - macrocin O-methyltransferase

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The expected taxonomic range for this enzyme is: Streptomyces fradiae

EC NUMBER
COMMENTARY hide
2.1.1.101
-
RECOMMENDED NAME
GeneOntology No.
macrocin O-methyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + macrocin = S-adenosyl-L-homocysteine + tylosin
show the reaction diagram
also converts lactenosin into desmycocin. Not identical with EC 2.1.1.102 demethylmacrocin O-methyltransferase; the 3-hydroxyl group of a 2-O-methyl-6-deoxy-D-allose residue in the macrolide antibiotic macrosin acts as methyl acceptor
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-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
methyl group transfer
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
tylosin biosynthesis
-
-
Biosynthesis of 12-, 14- and 16-membered macrolides
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Biosynthesis of antibiotics
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SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:macrocin 3'''-O-methyltransferase
Requires Mg2+, Mn2+ or Co2+. The 3-hydroxy group of the 2-O-methyl-6-deoxy-D-allose moiety in the macrolide antibiotic macrosin acts as methyl acceptor, generating tylosin, another macrolide antibiotic. Isolated from the bacterium Streptomyces fradiae. Not identical with EC 2.1.1.102, demethylmacrocin O-methyltransferase.
CAS REGISTRY NUMBER
COMMENTARY hide
79468-52-3
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
S-adenosyl-L-methionine + 20-dihydrolactenocin
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + dihydromacrocin
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + lactenocin
S-adenosyl-L-homocysteine + desmycosin
show the reaction diagram
S-adenosyl-L-methionine + macrocin
S-adenosyl-L-homocysteine + tylosin
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + macrocin
S-adenosylhomocysteine + tylosin
show the reaction diagram
additional information
?
-
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demethylmacrocin, demethyllactenocin, N5-methyltetrahydrofolate, betaine, choline, methylthioadenosine and methionine are not substrates
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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
S-adenosyl-L-methionine + macrocin
S-adenosylhomocysteine + tylosin
show the reaction diagram
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Fe2+
-
stimulated by iron (II) sulfate
Zn2+
-
stimulated by zinc sulfate
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
demethyllactenocin
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Demethylmacrocin
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-
Desmycosin
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weak inhibition
Relomycin
S-adenosyl-L-homocysteine
sinefungin
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competitive inhibition, potent inhibitor
tylosin
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.007
lactenocin
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-
0.005 - 0.033
macrocin
0.022 - 0.029
S-adenosyl-L-methionine
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.006
4'-demethyllactenocin
-
-
0.005
Demethylmacrocin
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-
0.023 - 0.026
Desmycosin
0.008 - 0.025
S-adenosyl-L-homocysteine
0.00006 - 0.00025
sinefungin
0.079 - 0.217
tylosin
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
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2 * 32000, SDS-PAGE
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4°C, enzyme is unstable, about 30% activity remains after 3 h
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4°C, quite stable in presence of 0.2 mM S-adenosyl-L-methionine and 10% ethanol, pH 7.0, stable over 6 months
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4°C, very stable for 3 h in presence of 10% ethanol
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
agriculture
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tylosin is used in the swine industry as a growth promotant
pharmacology