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
ECTree
2.1.1.292 carminomycin 4-O-methyltransferaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 2.1.1.292 - carminomycin 4-O-methyltransferase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
S-adenosyl-L-methionine + 10-carboxy-13-deoxycarminomycin
S-adenosyl-L-homocysteine + 10-carboxy-13-deoxydaunorubicin
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?
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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-
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?
S-adenosyl-L-methionine + 13-deoxycarminomycin
S-adenosyl-L-homocysteine + 13-deoxydaunorubicin
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-
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?
S-adenosyl-L-methionine + 13-dihydrocarminomycin
S-adenosyl-L-homocysteine + 13-dihydrodaunomycin
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?
S-adenosyl-L-methionine + 13-dihydrocarminomycin
S-adenosyl-L-homocysteine + daunorubicinol
S-adenosyl-L-methionine + 15-demethoxy-aclacinomycin T
S-adenosyl-L-homocysteine + 4-O-methyl-15-decarboxyaclacinomycin T
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-
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?
S-adenosyl-L-methionine + 2-chloro-4-nitrophenol
S-adenosyl-L-homocysteine + methyl-2-chloro-4-nitrophenol
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?
S-adenosyl-L-methionine + aclacinomycin T
S-adenosyl-L-homocysteine + triglycosylated aclacinomycin A
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?
S-adenosyl-L-methionine + rhodomycin D
S-adenosyl-L-homocysteine + 4-O-methoxyrhodomycin D
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?
S-adenosyl-[(3S)-3-amino-3-(1H-tetrazol-5-yl)propyl](methyl)sulfanium + 2-chloro-4-nitrophenol
S-adenosyl-(3S)-3-amino-3-(1H-tetrazol-5-yl)propane-1-thiol + methyl-2-chloro-4-nitrophenol
S-adenosyl-[(3S)-3-amino-3-(1H-tetrazol-5-yl)propyl](methyl)sulfanium is a derivative of AdoMet (S-adenosyl-L-methionine)
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?
S-adenosyl-L-methionine + 13-dihydrocarminomycin
S-adenosyl-L-homocysteine + daunorubicinol
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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 + 13-dihydrocarminomycin
S-adenosyl-L-homocysteine + daunorubicinol
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the enzyme shows a slightly higher affinity for carminomycin than for 13-dihydrocarminomycin
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?
S-adenosyl-L-methionine + carminomycin
S-adenosyl-L-homocysteine + daunomycin
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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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?
S-adenosyl-L-methionine + carminomycin
S-adenosyl-L-homocysteine + daunorubicin
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?
S-adenosyl-L-methionine + carminomycin
S-adenosyl-L-homocysteine + daunorubicin
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?
S-adenosyl-L-methionine + carminomycin
S-adenosyl-L-homocysteine + daunorubicin
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?
S-adenosyl-L-methionine + carminomycin
S-adenosyl-L-homocysteine + daunorubicin
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the enzyme shows a slightly higher affinity for carminomycin than for 13-dihydrocarminomycin
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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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additional information
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the enzyme has been reported to methylate various modified anthracyclines and flavonoids as surrogate substrates. 2-Chloro-4-nitrophenol is a substrate of DnrK. High-throughput DnrK colorimetric assay with the surrogate acceptor 2-chloro-4-nitrophenol and the different cosubstrates. No activity with derivative S-(7-deazaadenosyl)-[(3S)-3-amino-3-(1H-tetrazol-5-yl)propyl](methyl)sulfanium
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additional information
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the purified enzyme does not catalyse methylation of the aglycones carminomycinone or 13-dihydrocarminomycinone
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?
