2.1.1.292: carminomycin 4-O-methyltransferase
This is an abbreviated version!
For detailed information about carminomycin 4-O-methyltransferase, go to the full flat file.
Word Map on EC 2.1.1.292
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2.1.1.292
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methyltransferases
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sam-dependent
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s-adenosyl-l-homocysteine
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daunorubicin
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peucetius
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s-adenosyl-l-methionine-dependent
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synthesis
- 2.1.1.292
- methyltransferases
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sam-dependent
- s-adenosyl-l-homocysteine
- daunorubicin
- peucetius
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s-adenosyl-l-methionine-dependent
- synthesis
Reaction
Synonyms
4-O-methyltransferase, anthracycline 4-O-methyltransferase, anthracycline methyltransferase, carminomycin 4-OMT, class I methyltransferase, COMT, DauK, DnrK
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Natural Substrates Products
Natural Substrates Products on EC 2.1.1.292 - carminomycin 4-O-methyltransferase
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REACTION DIAGRAM
S-adenosyl-L-methionine + 11-deoxy-beta-rhodomycin T
S-adenosyl-L-homocysteine + 4-O-methyl-11-deoxy-beta-rhodomycin T
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S-adenosyl-L-methionine + 13-dihydrocarminomycin
S-adenosyl-L-homocysteine + daunorubicinol
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terminal enzyme in the daunomycin biosynthesis pathway
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S-adenosyl-L-methionine + 15-demethoxy-aclacinomycin T
S-adenosyl-L-homocysteine + 4-O-methyl-15-decarboxyaclacinomycin T
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S-adenosyl-L-methionine + carminomycin
S-adenosyl-L-homocysteine + daunomycin
with the corresponding aglycones, carminomycinone and 13-dihydrocarminomycinone, as substrates, no methylated products are detected. Other 4-hydroxyanthracyclines such as aklavin and aclacinomycin A, and 4-hydroxyanthracyclinones such as erhodomycinone and aklavinone, are not substrates for the 4-O-methyltransferase. These reaction specificities indicate that glycosylation of the anthracyclinone molecule must occur before 4-O-methylation, which means that 4-O-methylation of carminomycin is probably the terminal step in the biosynthesis of daunomycin, and that daunomycinone is not an intermediate in the pathway
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additional information
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the enzyme possesses rather relaxed substrate specificity in regard to modifications in the polyaromatic anthracycline ring system, but it is quite specific with respect to the length of the carbohydrate chain at C-7, accepting only monoglycosides. In addition, DnrK has even been shown to be able to methylate various flavonoids. Discovery of a 10-decarboxylation activity of DnrK
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S-adenosyl-L-homocysteine + daunorubicin
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S-adenosyl-L-methionine + carminomycin
S-adenosyl-L-homocysteine + daunorubicin
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