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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

Reaction

S-adenosyl-L-methionine
+
carminomycin
=
S-adenosyl-L-homocysteine
+
daunorubicin

Synonyms

4-O-methyltransferase, anthracycline 4-O-methyltransferase, anthracycline methyltransferase, carminomycin 4-OMT, class I methyltransferase, COMT, DauK, DnrK

ECTree

     2 Transferases
         2.1 Transferring one-carbon groups
             2.1.1 Methyltransferases
                2.1.1.292 carminomycin 4-O-methyltransferase

Natural Substrates Products

Natural Substrates Products on EC 2.1.1.292 - carminomycin 4-O-methyltransferase

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NATURAL SUBSTRATE
NATURAL 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 + 11-deoxy-beta-rhodomycin T
S-adenosyl-L-homocysteine + 4-O-methyl-11-deoxy-beta-rhodomycin T
show the reaction diagram
-
-
-
?
S-adenosyl-L-methionine + 13-dihydrocarminomycin
S-adenosyl-L-homocysteine + daunorubicinol
show the reaction diagram
-
terminal enzyme in the daunomycin biosynthesis pathway
-
-
?
S-adenosyl-L-methionine + 15-demethoxy-aclacinomycin T
S-adenosyl-L-homocysteine + 4-O-methyl-15-decarboxyaclacinomycin T
show the reaction diagram
-
-
-
?
S-adenosyl-L-methionine + carminomycin
S-adenosyl-L-homocysteine + daunomycin
show the reaction diagram
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
-
-
?
S-adenosyl-L-methionine + carminomycin
S-adenosyl-L-homocysteine + daunorubicin
show the reaction diagram
additional information
?
-
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
-
-
-