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Literature summary extracted from

  • Dickens, M.L.; Priestley, N.D.; Strohl, W.R.
    In vivo and in vitro bioconversion of epsilon-rhodomycinone glycoside to doxorubicin: functions of DauP, DauK, and DoxA (1997), J. Bacteriol., 179, 2641-2650.
    View publication on PubMedView publication on EuropePMC

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.13.181 13-deoxycarminomycin + NADPH + H+ + O2 Streptomyces sp. DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin 13-dihydrocarminomycin + NADP+ + H2O
-
?
1.14.13.181 13-deoxydaunorubicin + NADPH + H+ + O2 Streptomyces sp. DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin 13-dihydrodaunorubicin + NADP+ + H2O
-
?
1.14.13.181 13-dihydrocarminomycin + NADPH + H+ + O2 Streptomyces sp. DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin carminomycin + NADP+ + H2O
-
?
1.14.13.181 13-dihydrodaunorubicin + NADPH + H+ + O2 Streptomyces sp. DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin daunorubicin + NADP+ + 2 H2O
-
?
1.14.13.181 daunomycin + NADPH + H+ + O2 Streptomyces sp. DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and 13-dihydrodaunorubicin and the hydroxylation at C-14 of daunorubicin doxorubicin + NADP+ + H2O
-
?

Organism

EC Number Organism UniProt Comment Textmining
1.14.13.181 Streptomyces sp. Q59971
-
-
2.1.1.292 Streptomyces sp.
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.13.181 13-deoxycarminomycin + NADPH + H+ + O2
-
Streptomyces sp. 13-dihydrocarminomycin + NADP+ + H2O
-
?
1.14.13.181 13-deoxycarminomycin + NADPH + H+ + O2 DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin Streptomyces sp. 13-dihydrocarminomycin + NADP+ + H2O
-
?
1.14.13.181 13-deoxydaunorubicin + NADPH + H+ + O2
-
Streptomyces sp. 13-dihydrodaunorubicin + NADP+ + H2O i.e. daunorubicinol ?
1.14.13.181 13-deoxydaunorubicin + NADPH + H+ + O2 DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin Streptomyces sp. 13-dihydrodaunorubicin + NADP+ + H2O
-
?
1.14.13.181 13-dihydrocarminomycin + NADPH + H+ + O2
-
Streptomyces sp. carminomycin + NADP+ + H2O
-
?
1.14.13.181 13-dihydrocarminomycin + NADPH + H+ + O2 DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin Streptomyces sp. carminomycin + NADP+ + H2O
-
?
1.14.13.181 13-dihydrodaunorubicin + NADPH + H+ + O2 DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin Streptomyces sp. daunorubicin + NADP+ + 2 H2O
-
?
1.14.13.181 13-dihydrodaunorubicin + NADPH + H+ + O2 i.e. daunorubicinol Streptomyces sp. daunorubicin + NADP+ + 2 H2O
-
?
1.14.13.181 daunomycin + NADPH + H+ + O2
-
Streptomyces sp. doxorubicin + NADP+ + H2O
-
?
1.14.13.181 daunomycin + NADPH + H+ + O2 DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and 13-dihydrodaunorubicin and the hydroxylation at C-14 of daunorubicin Streptomyces sp. doxorubicin + NADP+ + H2O
-
?
2.1.1.292 S-adenosyl-L-methionine + 10-carboxy-13-deoxycarminomycin
-
Streptomyces sp. S-adenosyl-L-homocysteine + 10-carboxy-13-deoxydaunorubicin
-
?
2.1.1.292 S-adenosyl-L-methionine + 13-deoxycarminomycin
-
Streptomyces sp. S-adenosyl-L-homocysteine + 13-deoxydaunorubicin
-
?
2.1.1.292 S-adenosyl-L-methionine + 13-dihydrocarminomycin
-
Streptomyces sp. S-adenosyl-L-homocysteine + 13-dihydrodaunomycin
-
?
2.1.1.292 S-adenosyl-L-methionine + carminomycin
-
Streptomyces sp. S-adenosyl-L-homocysteine + daunorubicin
-
?
2.1.1.292 S-adenosyl-L-methionine + rhodomycin D
-
Streptomyces sp. S-adenosyl-L-homocysteine + 4-O-methoxyrhodomycin D
-
?

Synonyms

EC Number Synonyms Comment Organism
1.14.13.181 DoxA
-
Streptomyces sp.
2.1.1.292 anthracycline 4-O-methyltransferase
-
Streptomyces sp.
2.1.1.292 DauK
-
Streptomyces sp.

Cofactor

EC Number Cofactor Comment Organism Structure
1.14.13.181 NADPH reduced flavin adenine dinucleotide, reduced flavin mononucleotide, and NADH do not substitute for NADPH in these reactions Streptomyces sp.