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Chemical Compound Review:

C00744 2- [(2R,3R,9R,11R,12R,13S,14R)- 12-[(2S,3R...

Synonyms:

Bauer, N.J. et al., Kreuzman, A.J. et al., Baltz, R.H. et al., Zuzulova, M. et al., Yeh, W.K. et al.

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Disease relevance of C00744

S-Adenosyl-L-methionine:demethylmacrocin O-methyltransferase catalyzes the conversion of demethylmacrocin to macrocin as the penultimate step of tylosin biosynthesis in Streptomyces fradiae [1].

High impact information on C00744

5. The enzyme required Mg2+, Mn2+, or Co2+ for maximal activity and was catalytically optimal at pH 7.5-8.0 and 31 degrees C. The O-methyltransferase catalyzed the conversion of macrocin to tylosin at a stoichiometric ratio of 1:1 [2].
0. The enzyme required Mg2+ for maximal activity and was catalytically optimal at pH 7.8-8.5 and 42 degrees C. The O-methyltransferase catalyzed conversion of demethylmacrocin to macrocin at a stoichiometric ratio of 1:1 [1].
A high-performance liquid chromatographic (HPLC) procedure was developed to assay S-adenosyl-L-methionine: macrocin O-methyltransferase [3].
We have shown that a mutant blocked in hydroxylation of the C-20 methyl group is also blocked in the further dehydrogenation of the C-20 hydroxymethyl group to a formyl group, and have confirmed in in vitro studies that the 2"'-O-methylation of demethylmacrocin must proceed the 3"'-O-methylation of macrocin to produce tylosin [4].
Antimicrobial activity of tylosin (CAS 1401-69-0) and five other 16-membered macrolides biosynthesized by Streptomyces fradiae (lactenocin, desmycosin, macrosin (CAS 11049-15-3), relomycin (CAS 1404-48-4) and 5-O-mycaminosyl tylonolide) against Ureaplasma urealyticum was studied [5].

Chemical compound and disease context of C00744

S-Adenosyl-L-methionine:macrocin O-methyltransferase catalyzes conversion of macrocin to tylosin, the terminal and main rate-limiting step of tylosin biosynthesis in Streptomyces fradiae [2].

References

Two distinctive O-methyltransferases catalyzing penultimate and terminal reactions of macrolide antibiotic (tylosin) biosynthesis. Substrate specificity, enzyme inhibition, and kinetic mechanism. Kreuzman, A.J., Turner, J.R., Yeh, W.K. J. Biol. Chem. (1988) [Pubmed]
Purification, characterization, and kinetic mechanism of S-adenosyl-L-methionine:macrocin O-methyltransferase from Streptomyces fradiae. Bauer, N.J., Kreuzman, A.J., Dotzlaf, J.E., Yeh, W.K. J. Biol. Chem. (1988) [Pubmed]
High-performance liquid chromatographic assay for S-adenosyl-L-methionine: macrocin O-methyltransferase. Yeh, W.K., Bauer, N.J., Dotzlaf, J.E. J. Chromatogr. (1984) [Pubmed]
Biosynthesis of the macrolide antibiotic tylosin. A preferred pathway from tylactone to tylosin. Baltz, R.H., Seno, E.T., Stonesifer, J., Wild, G.M. J. Antibiot. (1983) [Pubmed]
In vitro activity of tylosin and its derivatives against Ureaplasma urealyticum. Zuzulova, M., Kleinova, D., Proksa, B., Fuska, J. Arzneimittel-Forschung. (1995) [Pubmed]

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