Information on EC 2.1.1.101 - macrocin O-methyltransferase

Word Map on EC 2.1.1.101
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The expected taxonomic range for this enzyme is: Streptomyces fradiae

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EC NUMBER
COMMENTARY hide
2.1.1.101
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RECOMMENDED NAME
GeneOntology No.
macrocin O-methyltransferase
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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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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
methyl group transfer
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of 12-, 14- and 16-membered macrolides
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Biosynthesis of antibiotics
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tylosin biosynthesis
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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.
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CAS REGISTRY NUMBER
COMMENTARY hide
79468-52-3
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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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
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?
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
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Fe2+
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stimulated by iron (II) sulfate
Zn2+
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stimulated by zinc sulfate
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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
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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
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.006
4'-demethyllactenocin
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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
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
32000
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2 * 32000, SDS-PAGE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
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2 * 32000, SDS-PAGE
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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
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
agriculture
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tylosin is used in the swine industry as a growth promotant
pharmacology
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LINKS TO OTHER DATABASES (specific for EC-Number 2.1.1.101)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
SYSTERS
Protein Mutant Database
InterPro (database of protein families, domains and functional sites)