KEGG   ENZYME: 1.14.13.231Help
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
BRITE hierarchy
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
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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
ec01130  Biosynthesis of antibiotics
Orthology
K18221  tetracycline 11a-monooxygenase, tetracycline resistance protein
Genes
PARC: CI960_14115
RAR: RIA_0365 RIA_0369
RAG: B739_0030 B739_0035
RAE: G148_1767 G148_1777
RAT: M949_0459
MOD: AS202_10870
CTAK: 4412677_02215(kmo)
Taxonomy
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

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