KEGG   ENZYME: 1.14.13.234Help
Entry
EC 1.14.13.234              Enzyme                                 

Name
5a,11a-dehydrotetracycline 5-monooxygenase;
oxyS (gene name);
12-dehydrotetracycline 5-monooxygenase
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
5a,11a-dehydrotetracycline,NADPH:oxygen oxidoreductase (5-hydroxylating)
Reaction(IUBMB)
5a,11a-dehydrotetracycline + NADPH + H+ + O2 = 5a,11a-dehydrooxytetracycline + NADP+ + H2O [RN:R09198]
Reaction(KEGG)
Substrate
5a,11a-dehydrotetracycline [CPD:C03206];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007]
Product
5a,11a-dehydrooxytetracycline [CPD:C18296];
NADP+ [CPD:C00006];
H2O [CPD:C00001]
Comment
The enzyme, characterized from the bacterium Streptomyces rimosus, is bifunctional, catalysing two successive monooxygenation reactions. It starts by catalysing the stereospecific hydroxylation of anhydrotetracycline at C-6 (EC 1.14.13.38). If the released product is captured by EC 1.3.98.4, 5a,11a-dehydrotetracycline dehydrogenase (OxyR), it is reduced to tetracycline. However, if the released product is recaptured by OxyS, it performs an additional hydroxylation at C-5, producing 5a,11a-dehydrooxytetracycline, which, following the action of OxyR, becomes oxytetracycline.
History
EC 1.14.13.234 created 2016
Pathway
ec00253  Tetracycline biosynthesis
ec01057  Biosynthesis of type II polyketide products
ec01100  Metabolic pathways
ec01130  Biosynthesis of antibiotics
Orthology
K14256  anhydrotetracycline 6-monooxygenase / 5a,11a-dehydrotetracycline 5-monooxygenase
Genes
KAU: B6264_18535
Taxonomy
Reference
1  [PMID:2914874]
  Authors
Binnie C, Warren M, Butler MJ
  Title
Cloning and heterologous expression in Streptomyces lividans of Streptomyces rimosus genes involved in oxytetracycline biosynthesis.
  Journal
J Bacteriol 171:887-95 (1989)
DOI:10.1128/JB.171.2.887-895.1989
Reference
2  [PMID:4959040]
  Authors
Miller PA, Saturnelli A, Martin JH, Itscher LA, Bohonos N
  Title
A new family of tetracycline precursors. N-demethylanhydrotetracyclines.
  Journal
Biochem Biophys Res Commun 16:285-91 (1964)
DOI:10.1016/0006-291X(64)90341-9
Reference
3  [PMID:3138982]
  Authors
Vancurova I, Volc J, Flieger M, Neuzil J, Novotna J, Vlach J, Behal V
  Title
Isolation of pure anhydrotetracycline oxygenase from Streptomyces aureofaciens.
  Journal
Biochem J 253:263-7 (1988)
Reference
4  [PMID:23621493]
  Authors
Wang P, Bashiri G, Gao X, Sawaya MR, Tang Y
  Title
Uncovering the enzymes that catalyze the final steps in oxytetracycline biosynthesis.
  Journal
J Am Chem Soc 135:7138-41 (2013)
DOI:10.1021/ja403516u
Other DBs
ExplorEnz - The Enzyme Database: 1.14.13.234
IUBMB Enzyme Nomenclature: 1.14.13.234
ExPASy - ENZYME nomenclature database: 1.14.13.234
BRENDA, the Enzyme Database: 1.14.13.234

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