KEGG ENZYME: 1.14.13.231

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

Tetracycline biosynthesis

Biosynthesis of secondary metabolites

Orthology

tetracycline 11a-monooxygenase, tetracycline resistance protein

Genes

F1325_16090(tet(X))

F9282_16570(tet(X))

DCE:	O6P33_04460(tet(X))

ATG:	J4G44_12795

MZO21_09705 MZO21_13965

Q3V95_09630

CI960_14115

CHF:	KTO58_07930

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))

4412677_02215(kmo)

MTP09_11285(tet(X)) MTP09_11315

CHRYMOREF3P_1011

F7R58_01260(tet(X))

EBV:	F0358_17055(tet(X)) F0358_17090(tet(X)) F0358_17245(tet(X))

FH779_17525(tet(X))

HNV03_01140(tet(X)) HNV03_01225(tet(X)) HNV03_01240(tet(X))

BPO_2231 BPO_2249 BPO_2256

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:

IUBMB Enzyme Nomenclature:

ExPASy - ENZYME nomenclature database:

BRENDA, the Enzyme Database:

DBGET integrated database retrieval system