KEGG   ORTHOLOGY: K14252
Entry
K14252                      KO                                     
Symbol
oxyL
Name
6-methylpretetramide 4-monooxygenase / 4-hydroxy-6-methylpretetramide 12a-monooxygenase [EC:1.14.13.232 1.14.13.233]
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
R05462  4-hydroxy-6-methylpretetramide,NADPH:oxygen oxidoreductase (12a-hydroxylating)
R09190  6-methylpretetramide,NADPH:oxygen oxidoreductase (4,12a-hydroxylating)
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   01057 Biosynthesis of type II polyketide products
    K14252  oxyL; 6-methylpretetramide 4-monooxygenase / 4-hydroxy-6-methylpretetramide 12a-monooxygenase
   00253 Tetracycline biosynthesis
    K14252  oxyL; 6-methylpretetramide 4-monooxygenase / 4-hydroxy-6-methylpretetramide 12a-monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   01008 Polyketide biosynthesis proteins
    K14252  oxyL; 6-methylpretetramide 4-monooxygenase / 4-hydroxy-6-methylpretetramide 12a-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
    1.14.13.232  6-methylpretetramide 4-monooxygenase
     K14252  oxyL; 6-methylpretetramide 4-monooxygenase / 4-hydroxy-6-methylpretetramide 12a-monooxygenase
    1.14.13.233  4-hydroxy-6-methylpretetramide 12a-monooxygenase
     K14252  oxyL; 6-methylpretetramide 4-monooxygenase / 4-hydroxy-6-methylpretetramide 12a-monooxygenase
Polyketide biosynthesis proteins [BR:ko01008]
 Polyketide tailoring proteins
  Oxygenase
   K14252  oxyL; 6-methylpretetramide 4-monooxygenase / 4-hydroxy-6-methylpretetramide 12a-monooxygenase
Other DBs
COG: COG0654
Genes
NAH: F5544_10695
SHY: SHJG_1193
SHO: SHJGH_1028
SBH: SBI_06866
SCI: B446_13470
SPRI: SPRI_0201 SPRI_7152
SPAV: Spa2297_32760
SGS: AVL59_46185
SGM: GCM10017557_73940
SPHW: NFX46_25010
SHUN: DWB77_05143(pcpB_4)
AORI: SD37_34185
KAL: KALB_7834
ACTU: Actkin_02482(pcpB_1)
AG: AAZ78335(oxyL)
 » show all
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
Zhang W, Watanabe K, Cai X, Jung ME, Tang Y, Zhan J
  Title
Identifying the minimal enzymes required for anhydrotetracycline biosynthesis.
  Journal
J Am Chem Soc 130:6068-9 (2008)
DOI:10.1021/ja800951e
Reference
  Authors
Wang P, Zhang W, Zhan J, Tang Y
  Title
Identification of OxyE as an ancillary oxygenase during tetracycline biosynthesis.
  Journal
Chembiochem 10:1544-50 (2009)
DOI:10.1002/cbic.200900122
LinkDB

KEGG   ENZYME: 1.14.13.233
Entry
EC 1.14.13.233              Enzyme                                 
Name
4-hydroxy-6-methylpretetramide 12a-monooxygenase;
oxyL (gene name)
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
4-hydroxy-6-methylpretetramide,NADPH:oxygen oxidoreductase (12a-hydroxylating)
Reaction(IUBMB)
4-hydroxy-6-methylpretetramide + NADPH + H+ + O2 = 4-de(dimethylamino)-4-oxoanhydrotetracycline + NADP+ + H2O [RN:R05462]
Reaction(KEGG)
R05462;
(other) R09190
Substrate
4-hydroxy-6-methylpretetramide [CPD:C06628];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007]
Product
4-de(dimethylamino)-4-oxoanhydrotetracycline [CPD:C06627];
NADP+ [CPD:C00006];
H2O [CPD:C00001]
Comment
Contains FAD. The enzyme, characterized from the bacterium Streptomyces rimosus, participates in the biosynthesis of tetracycline antibiotics. The enzyme is bifunctional, and can also catalyse EC 1.14.13.232, 6-methylpretetramide 4-monooxygenase.
History
EC 1.14.13.233 created 2016
Pathway
ec00253  Tetracycline biosynthesis
ec01057  Biosynthesis of type II polyketide products
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K14252  6-methylpretetramide 4-monooxygenase / 4-hydroxy-6-methylpretetramide 12a-monooxygenase
Genes
NAHF5544_10695
SHYSHJG_1193
SHOSHJGH_1028
SBHSBI_06866
SCIB446_13470
SPRISPRI_0201 SPRI_7152
SPAVSpa2297_32760
SGSAVL59_46185
SGMGCM10017557_73940
SPHWNFX46_25010
SGZC0216_31875
SVRCP971_24005
SGFHEP81_07938
SRIMCP984_02425
SPLACP981_34475
SHUNDWB77_05143(pcpB_4)
SXNIAG42_36430
SINEKI385_25240
SYANNRK68_34850
SVIOHWN34_29125
SSPNLXH13_14080
SDRZNEH16_32465
SHAUK9S39_12920
KAUB6264_18580
KISHUT16_23740
MIKFOE78_19175
AORISD37_34185
ARHDVSH64_28950
KALKALB_7834
KUTJJ691_15620
ACTUActkin_02482(pcpB_1)
CROSN8J89_20350
PLKCIK06_11100
DAURDaura_37895
CCAZCOUCH_15955
KBBccbrp13_21970
 » show all
Reference
1  [PMID:18422316]
  Authors
Zhang W, Watanabe K, Cai X, Jung ME, Tang Y, Zhan J
  Title
Identifying the minimal enzymes required for anhydrotetracycline biosynthesis.
  Journal
J Am Chem Soc 130:6068-9 (2008)
DOI:10.1021/ja800951e
Other DBs
ExplorEnz - The Enzyme Database: 1.14.13.233
IUBMB Enzyme Nomenclature: 1.14.13.233
ExPASy - ENZYME nomenclature database: 1.14.13.233
BRENDA, the Enzyme Database: 1.14.13.233
LinkDB

KEGG   REACTION: R05462
Entry
R05462                      Reaction                               
Name
4-hydroxy-6-methylpretetramide,NADPH:oxygen oxidoreductase (12a-hydroxylating)
Definition
4-Hydroxy-6-methylpretetramide + NADPH + Oxygen + H+ <=> 4-Keto-anhydrotetracycline + NADP+ + H2O
Equation
Comment
following after R05463
Reaction class
RC00001  C00005_C00006
RC01388  C06627_C06628
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
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
    1.14.13.233
     R05462  4-Hydroxy-6-methylpretetramide + NADPH + Oxygen + H+ <=> 4-Keto-anhydrotetracycline + NADP+ + H2O
Orthology
K14252  6-methylpretetramide 4-monooxygenase / 4-hydroxy-6-methylpretetramide 12a-monooxygenase [EC:1.14.13.232 1.14.13.233]
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:18422316]
  Authors
Zhang W, Watanabe K, Cai X, Jung ME, Tang Y, Zhan J
  Title
Identifying the minimal enzymes required for anhydrotetracycline biosynthesis.
  Journal
J Am Chem Soc 130:6068-9 (2008)
DOI:10.1021/ja800951e
Reference
3  [PMID:19472250]
  Authors
Wang P, Zhang W, Zhan J, Tang Y
  Title
Identification of OxyE as an ancillary oxygenase during tetracycline biosynthesis.
  Journal
Chembiochem 10:1544-50 (2009)
DOI:10.1002/cbic.200900122
Other DBs
RHEA: 50359
LinkDB

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