KEGG ORTHOLOGY: K14256

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

Reaction

R04060

anhydrotetracycline,NADPH:oxygen oxidoreductase (6-hydroxylating)

R09198

5a,11a-dehydrotetracycline,NADPH:oxygen oxidoreductase (5-hydroxylating)

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

GO:

0047670

Genes

SVR:	CP971_23960

SRIM:

SPLA:

SACT:

SDRZ:

SCYN:

SOV:	QZH56_28980

KAU:	B6264_18535

NEX:	NE857_24350

AGRA:

AGRA3207_005105 AGRA3207_005106

AORI:

SD37_34210

KUT:	JJ691_15570

CROS:

N8J89_05295

ACTL:

L3i22_066710

DAUR:

Daura_37815 Daura_37840

CCAZ:

COUCH_15960

AG:	AAZ78342(oxyS) AEI98657(ctcN) BAA07387(cts8)

» show all

Reference

PMID:16597959

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

[ag:AAZ78342]

Reference

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

Reference

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

All links

Ontology (4)   
   KEGG BRITE (3)   
   GO (1)   
Pathway (10)   
   KEGG PATHWAY (8)   
   KEGG MODULE (2)   
Chemical reaction (6)   
   KEGG ENZYME (2)   
   KEGG REACTION (2)   
   KEGG RCLASS (2)   
Gene (22)   
   KEGG GENES (21)   
   OC (1)   
Literature (3)   
   PubMed (3)   
All databases (45)   

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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

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

SVR:	CP971_23960

SRIM:

CP984_02460

SPLA:

CP981_34445

SACT:

DMT42_19730

SDRZ:

NEH16_31700

SCYN:

N8I84_06470

SOV:	QZH56_28980

KAU:	B6264_18535

NEX:	NE857_24350

AGRA:

AGRA3207_005105 AGRA3207_005106

AORI:

SD37_34210

KUT:	JJ691_15570

CROS:

N8J89_05295

ACTL:

L3i22_066710

DAUR:

Daura_37815 Daura_37840

CCAZ:

COUCH_15960

» show all

Reference

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

REACTION: R04060

Entry

R04060                      Reaction

Name

anhydrotetracycline,NADPH:oxygen oxidoreductase (6-hydroxylating)

Definition

Anhydrotetracycline + Oxygen + NADPH + H+ <=> 5a,11a-Dehydrotetracycline + NADP+ + H2O

Equation

C02811 + C00007 + C00005 + C00080 <=> C03206 + C00006 + C00001

Reaction class

RC00001

C00005_C00006

RC01062

C02811_C03206

Enzyme

1.14.13.38

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

Brite

Enzymatic reactions [BR:br08201]
1. Oxidoreductase reactions
  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
     R04060  Anhydrotetracycline + Oxygen + NADPH + H+ <=> 5a,11a-Dehydrotetracycline + NADP+ + H2O

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

All links

Ontology (1)   
   KEGG BRITE (1)   
Pathway (10)   
   KEGG PATHWAY (8)   
   KEGG MODULE (2)   
Chemical substance (7)   
   KEGG COMPOUND (7)   
Chemical reaction (3)   
   KEGG ENZYME (1)   
   KEGG RCLASS (2)   
Gene (22)   
   KEGG ORTHOLOGY (1)   
   KEGG GENES (21)   
All databases (43)   

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