KEGG   ENZYME: 1.14.13.181Help
Entry
EC 1.14.13.181              Enzyme                                 

Name
13-deoxydaunorubicin hydroxylase;
DoxA
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
BRITE hierarchy
Sysname
13-deoxydaunorubicin,NADPH:oxygen oxidoreductase (13-hydroxylating)
Reaction(IUBMB)
(1) 13-deoxydaunorubicin + NADPH + H+ + O2 = 13-dihydrodaunorubicin + NADP+ + H2O [RN:R06688];
(2) 13-dihydrodaunorubicin + NADPH + H+ + O2 = daunorubicin + NADP+ + 2 H2O [RN:R06689]
Reaction(KEGG)
Substrate
13-deoxydaunorubicin [CPD:C12429];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007];
13-dihydrodaunorubicin [CPD:C12430]
Product
13-dihydrodaunorubicin [CPD:C12430];
NADP+ [CPD:C00006];
H2O [CPD:C00001];
daunorubicin [CPD:C01907]
Comment
The enzymes from the Gram-positive bacteria Streptomyces sp. C5 and Streptomyces peucetius show broad substrate specificity for structures based on an anthracycline aglycone, but have a strong preference for 4-methoxy anthracycline intermediates (13-deoxydaunorubicin and 13-dihydrodaunorubicin) over their 4-hydroxy analogues (13-deoxycarminomycin and 13-dihydrocarminomycin), as well as a preference for substrates hydroxylated at the C-13 rather than the C-14 position.
History
EC 1.14.13.181 created 2013
Pathway
Biosynthesis of type II polyketide products
Biosynthesis of antibiotics
Orthology
K15955  
13-deoxydaunorubicin hydroxylase
Reference
1  [PMID:9864343]
  Authors
Walczak RJ, Dickens ML, Priestley ND, Strohl WR
  Title
Purification, properties, and characterization of recombinant Streptomyces sp. strain C5 DoxA, a cytochrome P-450 catalyzing multiple steps in doxorubicin biosynthesis.
  Journal
J. Bacteriol. 181 (1999) 298-304.
  Sequence
Reference
2  [PMID:9098063]
  Authors
Dickens ML, Priestley ND, Strohl WR.
  Title
In vivo and in vitro bioconversion of epsilon-rhodomycinone glycoside to doxorubicin: functions of DauP, DauK, and DoxA.
  Journal
J. Bacteriol. 179 (1997) 2641-50.
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 

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