KEGG   ORTHOLOGY: K14256
Entry
K14256                      KO                                     
Symbol
oxyS, cts8
Name
anhydrotetracycline 6-monooxygenase / 5a,11a-dehydrotetracycline 5-monooxygenase [EC:1.14.13.38 1.14.13.234]
Pathway
map00253  Tetracycline biosynthesis
map01057  Biosynthesis of type II polyketide products
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
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
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   01008 Polyketide biosynthesis proteins
    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
Polyketide biosynthesis proteins [BR:ko01008]
 Polyketide tailoring proteins
  Oxygenase
   K14256  oxyS, cts8; anhydrotetracycline 6-monooxygenase / 5a,11a-dehydrotetracycline 5-monooxygenase
Other DBs
RN: R04060 R09193 R09198
GO: 0047670
Genes
SVR: CP971_23960
SRIM: CP984_02460
SPLA: CP981_34445
SACT: DMT42_19730
KAU: B6264_18535
AGRA: AGRA3207_005105 AGRA3207_005106
AORI: SD37_34210
CCAZ: COUCH_15960
AG: AAZ78342(oxyS) AEI98657(ctcN) BAA07387(cts8)
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
LinkDB

KEGG   ENZYME: 1.14.13.38
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
Sysname
anhydrotetracycline,NADPH:oxygen oxidoreductase (6-hydroxylating)
Reaction(IUBMB)
anhydrotetracycline + NADPH + H+ + O2 = 12-dehydrotetracycline + NADP+ + H2O [RN:R04060]
Reaction(KEGG)
R04060;
(other) R09193
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
ec01110  Biosynthesis of secondary metabolites
Orthology
K14256  anhydrotetracycline 6-monooxygenase / 5a,11a-dehydrotetracycline 5-monooxygenase
Genes
SVRCP971_23960
SRIMCP984_02460
SPLACP981_34445
SACTDMT42_19730
KAUB6264_18535
AGRAAGRA3207_005105 AGRA3207_005106
AORISD37_34210
CCAZCOUCH_15960
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)
DOI:10.1042/bj2530263
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
LinkDB

KEGG   REACTION: R04060
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
rn01110  Biosynthesis of secondary metabolites
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]
Reference
1  [PMID:20522541]
  Authors
Pickens LB, Tang Y
  Title
Oxytetracycline biosynthesis.
  Journal
J Biol Chem 285:27509-15 (2010)
DOI:10.1074/jbc.R110.130419
Reference
2  [PMID:16148009]
  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
Other DBs
RHEA: 11979
LinkDB

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