KEGG   ORTHOLOGY: K14256Help
Entry
K14256                      KO                                     

Name
oxyS, cts8
Definition
anhydrotetracycline 6-monooxygenase / 5a,11a-dehydrotetracycline 5-monooxygenase [EC:1.14.13.38 1.14.13.234]
Pathway
ko00253  Tetracycline biosynthesis
ko01057  Biosynthesis of type II polyketide products
ko01100  Metabolic pathways
ko01130  Biosynthesis of antibiotics
Module
M00780  Tetracycline/oxytetracycline biosynthesis, pretetramide => tetracycline/oxytetracycline
M00823  Chlortetracycline biosynthesis, pretetramide => chlortetracycline
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   01057 Biosynthesis of type II polyketide products
    K14256  oxyS, cts8; anhydrotetracycline 6-monooxygenase / 5a,11a-dehydrotetracycline 5-monooxygenase
   00253 Tetracycline biosynthesis
    K14256  oxyS, cts8; anhydrotetracycline 6-monooxygenase / 5a,11a-dehydrotetracycline 5-monooxygenase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.13  With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.13.38  anhydrotetracycline 6-monooxygenase
     K14256  oxyS, cts8; anhydrotetracycline 6-monooxygenase / 5a,11a-dehydrotetracycline 5-monooxygenase
    1.14.13.234  5a,11a-dehydrotetracycline 5-monooxygenase
     K14256  oxyS, cts8; anhydrotetracycline 6-monooxygenase / 5a,11a-dehydrotetracycline 5-monooxygenase
BRITE hierarchy
Other DBs
RN: R04060 R09193 R09198
GO: 0047670
Genes
KAU: B6264_18535
AG: AAZ78342(oxyS) AEI98657(ctcN) BAA07387(cts8)
TaxonomyKoalaUniProt
Reference
  Authors
Zhang W, Ames BD, Tsai SC, Tang Y
  Title
Engineered biosynthesis of a novel amidated polyketide, using the malonamyl-specific initiation module from the oxytetracycline polyketide synthase.
  Journal
Appl Environ Microbiol 72:2573-80 (2006)
DOI:10.1128/AEM.72.4.2573-2580.2006
  Sequence
Reference
  Authors
Peric-Concha N, Borovicka B, Long PF, Hranueli D, Waterman PG, Hunter IS
  Title
Ablation of the otcC gene encoding a post-polyketide hydroxylase from the oxytetracyline biosynthetic pathway in Streptomyces rimosus results in novel polyketides with altered chain length.
  Journal
J Biol Chem 280:37455-60 (2005)
DOI:10.1074/jbc.M503191200
Reference
  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

KEGG   ENZYME: 1.14.13.38Help
Entry
EC 1.14.13.38               Enzyme                                 

Name
anhydrotetracycline 6-monooxygenase;
ATC oxygenase;
anhydrotetracycline oxygenase;
oxyS (gene name);
anhydrotetracycline 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
anhydrotetracycline,NADPH:oxygen oxidoreductase (6-hydroxylating)
Reaction(IUBMB)
anhydrotetracycline + NADPH + H+ + O2 = 12-dehydrotetracycline + NADP+ + H2O [RN:R04060]
Reaction(KEGG)
R04060;
(other) R09193
Show
Substrate
anhydrotetracycline [CPD:C02811];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007]
Product
12-dehydrotetracycline [CPD:C03206];
NADP+ [CPD:C00006];
H2O [CPD:C00001]
Comment
The enzyme, characterized from the bacterium Streptomyces rimosus, participates in the biosynthesis of tetracycline antibiotics. It can also catalyse EC 1.14.13.234, 12-dehydrotetracycline 5-monooxygenase.
History
EC 1.14.13.38 created 1990, modified 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
  Authors
Behal, V., Hostalek, Z. and Vanek, Z.
  Title
Anhydrotetracycline oxygenase activity and biosynthesis of tetracyclines in streptomyces aureofaciens.
  Journal
Biotechnol Lett 1:177-182 (1979)
Reference
2  [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
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: 1.14.13.38
IUBMB Enzyme Nomenclature: 1.14.13.38
ExPASy - ENZYME nomenclature database: 1.14.13.38
BRENDA, the Enzyme Database: 1.14.13.38
CAS: 70766-62-0

KEGG   REACTION: R04060Help
Entry
R04060                      Reaction                               

Name
anhydrotetracycline,NADPH:oxygen oxidoreductase (6-hydroxylating)
Definition
Anhydrotetracycline + Oxygen + NADPH + H+ <=> 5a,11a-Dehydrotetracycline + NADP+ + H2O
Equation
Reaction class
RC00001  C00005_C00006
RC01062  C02811_C03206
Enzyme
Pathway
rn00253  Tetracycline biosynthesis
rn01057  Biosynthesis of type II polyketide products
rn01100  Metabolic pathways
rn01130  Biosynthesis of antibiotics
Module
M00780  Tetracycline/oxytetracycline biosynthesis, pretetramide => tetracycline/oxytetracycline
M00823  Chlortetracycline biosynthesis, pretetramide => chlortetracycline
Orthology
K14256  anhydrotetracycline 6-monooxygenase / 5a,11a-dehydrotetracycline 5-monooxygenase [EC:1.14.13.38 1.14.13.234]
Other DBs
RHEA: 11979

DBGET integrated database retrieval system