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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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macrocin O-methyltransferase
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S-adenosyl-L-methionine + macrocin = S-adenosyl-L-homocysteine + tylosin
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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methyl group transfer
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Biosynthesis of 12-, 14- and 16-membered macrolides
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Biosynthesis of antibiotics
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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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macrocin methyltransferase
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S-adenosyl-L-methionine-macrocin O-methyltransferase
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brenda
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S-adenosyl-L-methionine + 20-dihydrolactenocin
S-adenosyl-L-homocysteine + ?
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S-adenosyl-L-methionine + dihydromacrocin
S-adenosyl-L-homocysteine + ?
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?
S-adenosyl-L-methionine + lactenocin
S-adenosyl-L-homocysteine + desmycosin
S-adenosyl-L-methionine + macrocin
S-adenosyl-L-homocysteine + tylosin
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S-adenosyl-L-methionine + macrocin
S-adenosylhomocysteine + tylosin
additional information
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demethylmacrocin, demethyllactenocin, N5-methyltetrahydrofolate, betaine, choline, methylthioadenosine and methionine are not substrates
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S-adenosyl-L-methionine + lactenocin
S-adenosyl-L-homocysteine + desmycosin
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S-adenosyl-L-methionine + lactenocin
S-adenosyl-L-homocysteine + desmycosin
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?
S-adenosyl-L-methionine + macrocin
S-adenosylhomocysteine + tylosin
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enzyme catalyzes 3'''-O-methylation of bound 2'''-O-methylated 6-deoxy-D-allose
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S-adenosyl-L-methionine + macrocin
S-adenosylhomocysteine + tylosin
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terminal and main rate-limiting step in tylosin biosynthesis
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S-adenosyl-L-methionine + macrocin
S-adenosylhomocysteine + tylosin
S-adenosyl-L-methionine + macrocin
S-adenosylhomocysteine + tylosin
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enzyme catalyzes 3'''-O-methylation of bound 2'''-O-methylated 6-deoxy-D-allose
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?
S-adenosyl-L-methionine + macrocin
S-adenosylhomocysteine + tylosin
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terminal and main rate-limiting step in tylosin biosynthesis
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?
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Fe2+
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stimulated by iron (II) sulfate
Zn2+
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stimulated by zinc sulfate
Co2+
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stimulated by cobalt chloride
Co2+
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can substitute Mg2+
Mg2+
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stimulated by magnesium sulfate
Mg2+
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required for maximal activity
Mn2+
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stimulated by manganese sulfate
Mn2+
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can substitute Mg2+
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Desmycosin
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weak inhibition
S-adenosyl-L-homocysteine
sinefungin
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competitive inhibition, potent inhibitor
Relomycin
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Relomycin
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weak inhibition
S-adenosyl-L-homocysteine
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S-adenosyl-L-homocysteine
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not D-enantiomer
tylosin
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tylosin
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weak inhibition
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0.022 - 0.029
S-adenosyl-L-methionine
0.005
macrocin
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0.022
S-adenosyl-L-methionine
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lactenocin as substrate
0.023
S-adenosyl-L-methionine
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macrocin as substrate
0.029
S-adenosyl-L-methionine
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0.006
4'-demethyllactenocin
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0.005
Demethylmacrocin
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0.008 - 0.025
S-adenosyl-L-homocysteine
0.00006 - 0.00025
sinefungin
0.023
Desmycosin
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fixed substrate S-adenosyl-L-methionine
0.026
Desmycosin
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fixed substrate macrocin
0.008
S-adenosyl-L-homocysteine
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fixed substrate macrocin
0.025
S-adenosyl-L-homocysteine
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fixed substrate S-adenosyl-L-methionine
0.00006
sinefungin
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0.079
tylosin
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fixed substrate S-adenosyl-L-methionine
0.217
tylosin
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fixed substrate lactenocin
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32000
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2 * 32000, SDS-PAGE
65000
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gel filtration
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dimer
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2 * 32000, SDS-PAGE
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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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agriculture
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tylosin is used in the swine industry as a growth promotant
pharmacology
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tylosin is used in veterinary medicine for treatment of infections caused by gram-positive bacteria and mycoplasma
pharmacology
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tylosin fermentation, antibiotic biosynthesis, enzyme catalyzes conversion of macrocin to tylosin in vivo
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TYLF_STRFR
256
28696
Swiss-Prot
A0A0B5SFK2_BACMY
281
32680
TrEMBL
A0A1V2MYI6_9ACTN
294
32709
TrEMBL
A0A1P8WSA3_9PLAN
234
26390
TrEMBL
A0A1V5QZ05_9BACT
352
40055
TrEMBL
A0A0D6T7B1_BACMY
281
32565
TrEMBL
Q63EF8_BACCZ
Bacillus cereus (strain ZK / E33L)
281
32545
TrEMBL
A9CZR5_HOEPD
Hoeflea phototrophica (strain DSM 17068 / NCIMB 14078 / DFL-43)
252
29287
TrEMBL
A0A0G8EDW4_BACCE
281
32501
TrEMBL
A0A1G4KUX0_BACCE
281
32558
TrEMBL
A0A0G8ESL2_BACCE
281
32593
TrEMBL
A0A0F0C2D1_9CLOT
293
32937
TrEMBL
M6QJ30_9LEPT
243
27860
TrEMBL
M6V8G5_9LEPT
252
29319
TrEMBL
N1LSK8_9BACI
271
31620
TrEMBL
A0A136K9E3_9BACT
270
30617
TrEMBL
H0E7A4_9ACTN
284
31813
TrEMBL
A0A1C4ANS3_BACCE
281
32500
TrEMBL
A0A1C4B734_BACCE
281
32468
TrEMBL
Q81GJ3_BACCR
Bacillus cereus (strain ATCC 14579 / DSM 31 / JCM 2152 / NBRC 15305 / NCIMB 9373 / NRRL B-3711)
281
32547
TrEMBL
A0A1V5NLJ7_9BACT
251
28312
TrEMBL
L8FL58_MYCSE
Mycobacterium smegmatis (strain MKD8)
266
30116
TrEMBL
A0A1V5VKK5_9BACT
227
26034
TrEMBL
A0A1Y5RS79_9RHOB
251
28490
TrEMBL
I7FWA8_MYCS2
Mycobacterium smegmatis (strain ATCC 700084 / mc(2)155)
266
30058
TrEMBL
A0A068N518_BACCE
265
30577
TrEMBL
A0A1Y5TLH8_9PROT
240
27165
TrEMBL
A0A1P8WKV1_9PLAN
247
27552
TrEMBL
A0A1D3RDS5_BACCE
281
32472
TrEMBL
A0A1D3NUH8_BACCE
281
32497
TrEMBL
N1LVH4_9BACI
281
32463
TrEMBL
D5PHK1_9MYCO
263
29446
TrEMBL
A0A0P1HRA9_9RHOB
242
27616
TrEMBL
A0A1V5QXG7_9PROT
645
73957
TrEMBL
A0A0J9E793_9RHOB
73
8268
TrEMBL
A0A1V5YQE9_9BACT
262
29689
TrEMBL
Q6HLX5_BACHK
Bacillus thuringiensis subsp. konkukian (strain 97-27)
281
32517
TrEMBL
A0A164Q984_BACCE
281
32472
TrEMBL
A0A1J5QN65_9ZZZZ
246
27672
TrEMBL
A0A1X6QHX4_BACMY
281
32655
TrEMBL
A0A1B9EK59_9ACTN
292
32500
TrEMBL
A4F7H0_SACEN
Saccharopolyspora erythraea (strain ATCC 11635 / DSM 40517 / JCM 4748 / NBRC 13426 / NCIMB 8594 / NRRL 2338)
270
30722
TrEMBL
A0QPG3_MYCS2
Mycobacterium smegmatis (strain ATCC 700084 / mc(2)155)
240
26990
TrEMBL
A0A110AWI1_9CYAN
1508
167879
TrEMBL
T2INC9_CROWT
201
22425
TrEMBL
A0A1C4BHM2_BACCE
281
32533
TrEMBL
A0A158ATE2_9BURK
252
28266
TrEMBL
A0A1C4B5J9_BACCE
281
32499
TrEMBL
A0A1Y5RU55_9PROT
258
28831
TrEMBL
A0A0P1H3Y7_9RHOB
252
28013
TrEMBL
M1QS96_BACTU
281
32560
TrEMBL
A0A0D6G5F8_MYCSM
266
29860
TrEMBL
A0A177HF78_9ACTN
226
25117
TrEMBL
D5PHJ8_9MYCO
267
30153
TrEMBL
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Seno, E.T.; Baltz, R.H.
Properties of S-adenosyl-L-methionine:macrocin O-methyltransferase in extracts of Streptomyces fradiae strains which produce normal or elevated levels of tylosin and in mutants blocked in specific O-methylations
Antimicrob. Agents Chemother.
20
370-377
1981
Streptomyces fradiae
brenda
Bauer, N.J.; Kreuzman, A.J.; Dotzlaf, J.E.; Yeh, W.K.
Purification, characterization, and kinetic mechanism of S-adenosyl-L-methionine:macrocin O-methyltransferase from Streptomyces fradiae
J. Biol. Chem.
263
15619-15625
1988
Streptomyces fradiae
brenda
Yeh, W.K.; Bauer, N.J.; Dotzlaf, J.E.
High-performance liquid chromatographic assay for S-adenosyl-L-methionine: macrocin O-methyltransferase
J. Chromatogr.
288
157-165
1984
Streptomyces fradiae
brenda
Kreuzman, A.J.; Turner, J.R.; Yeh, W.K.
Two distinctive O-methyltransferases catalyzing penultimate and terminal reactions of macrolide antibiotic (tylosin) biosynthesis. Substrate specificity, enzyme inhibition, and kinetic mechanism
J. Biol. Chem.
263
15626-15633
1988
Streptomyces fradiae
brenda
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