KEGG   ORTHOLOGY: K18221
Entry
K18221                      KO                                     
Symbol
tetX
Name
tetracycline 11a-monooxygenase, tetracycline resistance protein [EC:1.14.13.231]
Pathway
map00253  Tetracycline biosynthesis
map01110  Biosynthesis of secondary metabolites
Reaction
R11449  tetracycline,NADPH:oxygen oxidoreductase (11a-hydroxylating)
R11525  oxytetracycline,NADPH:oxygen oxidoreductase (11a-hydroxylating)
R11526  chlortetracycline,NADPH:oxygen oxidoreductase (11a-hydroxylating)
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   00253 Tetracycline biosynthesis
    K18221  tetX; tetracycline 11a-monooxygenase, tetracycline resistance protein
 09180 Brite Hierarchies
  09183 Protein families: signaling and cellular processes
   01504 Antimicrobial resistance genes
    K18221  tetX; tetracycline 11a-monooxygenase, tetracycline resistance protein
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
    1.14.13.231  tetracycline 11a-monooxygenase
     K18221  tetX; tetracycline 11a-monooxygenase, tetracycline resistance protein
Antimicrobial resistance genes [BR:ko01504]
 Gene variants
  Tetracycline resistance genes
   Others
    K18221  tetX; tetracycline 11a-monooxygenase, tetracycline resistance protein
Other DBs
COG: COG0654
Genes
PCOL: F1325_16090(tet(X))
PCIB: F9282_16570(tet(X))
DCE: O6P33_04460(tet(X))
ATG: J4G44_12795
APOT: MZO21_09705 MZO21_13965
AALN: Q3V95_09630
PARC: CI960_14115
CHF: KTO58_07930
CHIM: CK934_21085
SFAE: MUK51_21330
MOD: AS202_10870 AS202_15215 AS202_20005
RAR: RIA_0365 RIA_0369
RAG: B739_0030 B739_0035
RAE: G148_1767 G148_1777
RAT: M949_0459
RCL: NYR17_04260(tet(X))
CTAK: 4412677_02215(kmo)
CSUP: MTP09_11285(tet(X)) MTP09_11315
CHRJ: CHRYMOREF3P_1011
CHRA: F7R58_01260(tet(X))
CHRD: KYG33_06290
CHRP: G6R40_02830(tet(X)) G6R40_07685(tet(X))
CHRK: KCF3NO3_45460
EBV: F0358_17055(tet(X)) F0358_17090(tet(X)) F0358_17245(tet(X))
EFAL: FH779_17525(tet(X))
ESTE: HNV03_01140(tet(X)) HNV03_01225(tet(X)) HNV03_01240(tet(X))
BPOR: BPO_2231 BPO_2249 BPO_2256
AG: AAA27471(tet(X))
 » show all
Reference
PMID:1846135
  Authors
Speer BS, Bedzyk L, Salyers AA
  Title
Evidence that a novel tetracycline resistance gene found on two Bacteroides transposons encodes an NADP-requiring oxidoreductase.
  Journal
J Bacteriol 173:176-83 (1991)
DOI:10.1128/JB.173.1.176-183.1991
  Sequence
[ag:AAA27471]
Reference
PMID:15452119
  Authors
Yang W, Moore IF, Koteva KP, Bareich DC, Hughes DW, Wright GD
  Title
TetX is a flavin-dependent monooxygenase conferring resistance to tetracycline antibiotics.
  Journal
J Biol Chem 279:52346-52 (2004)
DOI:10.1074/jbc.M409573200
Reference
PMID:19862477
  Authors
Thaker M, Spanogiannopoulos P, Wright GD
  Title
The tetracycline resistome.
  Journal
Cell Mol Life Sci 67:419-31 (2010)
DOI:10.1007/s00018-009-0172-6
Reference
PMID:19187139
  Authors
Ghosh S, Sadowsky MJ, Roberts MC, Gralnick JA, LaPara TM
  Title
Sphingobacterium sp. strain PM2-P1-29 harbours a functional tet(X) gene encoding for the degradation of tetracycline.
  Journal
J Appl Microbiol 106:1336-42 (2009)
DOI:10.1111/j.1365-2672.2008.04101.x
LinkDB

KEGG   ENZYME: 1.14.13.231
Entry
EC 1.14.13.231              Enzyme                                 
Name
tetracycline 11a-monooxygenase;
tetX (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
tetracycline,NADPH:oxygen oxidoreductase (11a-hydroxylating)
Reaction(IUBMB)
tetracycline + NADPH + H+ + O2 = 11a-hydroxytetracycline + NADP+ + H2O [RN:R11449]
Reaction(KEGG)
R11449;
(other) R11525 R11526
Substrate
tetracycline [CPD:C06570];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007]
Product
11a-hydroxytetracycline [CPD:C21391];
NADP+ [CPD:C00006];
H2O [CPD:C00001]
Comment
A flavoprotein (FAD). This bacterial enzyme confers resistance to all clinically relevant tetracyclines when expressed under aerobic conditions. The hydroxylated products are very unstable and lead to intramolecular cyclization and non-enzymic breakdown to undefined products.
History
EC 1.14.13.231 created 2016
Pathway
ec00253  Tetracycline biosynthesis
ec01110  Biosynthesis of secondary metabolites
Orthology
K18221  tetracycline 11a-monooxygenase, tetracycline resistance protein
Genes
PCOL: F1325_16090(tet(X))
PCIB: F9282_16570(tet(X))
DCE: O6P33_04460(tet(X))
ATG: J4G44_12795
APOT: MZO21_09705 MZO21_13965
AALN: Q3V95_09630
PARC: CI960_14115
CHF: KTO58_07930
CHIM: CK934_21085
SFAE: MUK51_21330
MOD: AS202_10870 AS202_15215 AS202_20005
RAR: RIA_0365 RIA_0369
RAG: B739_0030 B739_0035
RAE: G148_1767 G148_1777
RAT: M949_0459
RCL: NYR17_04260(tet(X))
CTAK: 4412677_02215(kmo)
CSUP: MTP09_11285(tet(X)) MTP09_11315
CHRJ: CHRYMOREF3P_1011
CHRA: F7R58_01260(tet(X))
CHRD: KYG33_06290
CHRP: G6R40_02830(tet(X)) G6R40_07685(tet(X))
CHRK: KCF3NO3_45460
EBV: F0358_17055(tet(X)) F0358_17090(tet(X)) F0358_17245(tet(X))
EFAL: FH779_17525(tet(X))
ESTE: HNV03_01140(tet(X)) HNV03_01225(tet(X)) HNV03_01240(tet(X))
BPOR: BPO_2231 BPO_2249 BPO_2256
 » show all
Reference
1  [PMID:15452119]
  Authors
Yang W, Moore IF, Koteva KP, Bareich DC, Hughes DW, Wright GD
  Title
TetX is a flavin-dependent monooxygenase conferring resistance to tetracycline antibiotics.
  Journal
J Biol Chem 279:52346-52 (2004)
DOI:10.1074/jbc.M409573200
Reference
2  [PMID:16128584]
  Authors
Moore IF, Hughes DW, Wright GD
  Title
Tigecycline is modified by the flavin-dependent monooxygenase TetX.
  Journal
Biochemistry 44:11829-35 (2005)
DOI:10.1021/bi0506066
Reference
3  [PMID:21402075]
  Authors
Volkers G, Palm GJ, Weiss MS, Wright GD, Hinrichs W
  Title
Structural basis for a new tetracycline resistance mechanism relying on the TetX  monooxygenase.
  Journal
FEBS Lett 585:1061-6 (2011)
DOI:10.1016/j.febslet.2011.03.012
Other DBs
ExplorEnz - The Enzyme Database: 1.14.13.231
IUBMB Enzyme Nomenclature: 1.14.13.231
ExPASy - ENZYME nomenclature database: 1.14.13.231
BRENDA, the Enzyme Database: 1.14.13.231
LinkDB

KEGG   REACTION: R11526
Entry
R11526                      Reaction                               
Name
chlortetracycline,NADPH:oxygen oxidoreductase (11a-hydroxylating)
Definition
Chlortetracycline + NADPH + H+ + Oxygen <=> 11a-Hydroxy-7-chlortetracycline + NADP+ + H2O
Equation
C06571 + C00005 + C00080 + C00007 <=> C21439 + C00006 + C00001
Reaction class
RC03438  C06571_C21439
Enzyme
1.14.13.231
Pathway
rn00253  Tetracycline biosynthesis
rn01110  Biosynthesis of secondary metabolites
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
    1.14.13.231
     R11526  Chlortetracycline + NADPH + H+ + Oxygen <=> 11a-Hydroxy-7-chlortetracycline + NADP+ + H2O
Orthology
K18221  tetracycline 11a-monooxygenase, tetracycline resistance protein [EC:1.14.13.231]
LinkDB

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