Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary for 1.14.13.231 extracted from

  • Yang, W.; Moore, I.F.; Koteva, K.P.; Bareich, D.C.; Hughes, D.W.; Wright, G.D.
    TetX is a flavin-dependent monooxygenase conferring resistance to tetracycline antibiotics (2004), J. Biol. Chem., 279, 52346-52352.
    View publication on PubMed
Search for more literature for 1.14.13.231

Cloned(Commentary)

Cloned (Comment) Organism
expression in Escherichia coli Bacteroides fragilis
expression in Escherichia coli Bacteroides thetaiotaomicron

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.0199
-
 demeclocycline pH 8.5 Bacteroides fragilis
0.02
-
 demeclocycline pH 8.5, temperature not specified in the publication Bacteroides thetaiotaomicron
0.028
-
 minocycline pH 8.5, temperature not specified in the publication Bacteroides thetaiotaomicron
0.0284
-
 minocycline pH 8.5 Bacteroides fragilis
0.054
-
 tetracycline pH 8.5 Bacteroides fragilis
0.054
-
 tetracycline pH 8.5, temperature not specified in the publication Bacteroides thetaiotaomicron
0.076
-
 oxytetracycline pH 8.5 Bacteroides fragilis
0.076
-
 alpha-doxycycline pH 8.5, temperature not specified in the publication Bacteroides thetaiotaomicron
0.0837
-
 doxycycline pH 8.5 Bacteroides fragilis
0.084
-
 doxycycline pH 8.5, temperature not specified in the publication Bacteroides thetaiotaomicron
0.11
-
 chlortetracycline pH 8.5 Bacteroides fragilis
0.11
-
 chlortetracycline pH 8.5, temperature not specified in the publication Bacteroides thetaiotaomicron
0.133
-
 NADPH pH 8.5 Bacteroides fragilis
0.133
-
 NADPH pH 8.5, temperature not specified in the publication Bacteroides thetaiotaomicron

Molecular Weight [Da]

Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
44000
-
 gel filtration Bacteroides fragilis

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
chlortetracycline + NADPH + H+ + O2 Bacteroides thetaiotaomicron
-
 11a-hydroxychlortetracycline + NADP+ + H2O
-
 ?
demeclocycline + NADPH + H+ + O2 Bacteroides thetaiotaomicron
-
 11a-hydroxydemeclocycline + NADP+ + H2O
-
 ?
doxycycline + NADPH + H+ + O2 Bacteroides thetaiotaomicron
-
 11a-hydroxydoxycycline + NADP+ + H2O
-
 ?
minocycline + NADPH + H+ + O2 Bacteroides thetaiotaomicron
-
 11a-hydroxyminocycline + NADP+ + H2O
-
 ?
additional information Bacteroides thetaiotaomicron the enzyme shows a broad tetracycline antibiotic spectrum and a requirement for molecular oxygen and NADPH in antibiotic degradation. The tetracycline products are unstable at neutral pH, but mass spectral and NMR characterization under acidic conditions support initial monohydroxylation at position 11a followed by intramolecular cyclization and non-enzymatic breakdown to other undefined products ?
-
 ?
tetracycline + NADPH + H+ + O2 Bacteroides thetaiotaomicron
-
 11a-hydroxytetracycline + NADP+ + H2O
-
 ?

Organism

Organism UniProt Comment Textmining
Bacteroides fragilis
-
-
-
Bacteroides thetaiotaomicron Q93L51
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant protein, purified protein gives a yellow solution Bacteroides fragilis

Reaction

Reaction Comment Organism Reaction ID
RH + [reduced NADPH-hemoprotein reductase] + O2 = ROH + [oxidized NADPH-hemoprotein reductase] + H2O tetracycline substrates, initial monohydroxylation at position 11a followed by intramolecular cyclization and non-enzymatic breakdown to undefined products Bacteroides fragilis
a

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
chlortetracycline + NADPH + H+ + O2
-
 Bacteroides thetaiotaomicron 11a-hydroxychlortetracycline + NADP+ + H2O
-
 ?
chlortetracycline + reduced flavoprotein + O2
-
 Bacteroides fragilis 11a-hydroxy-chlortetracycline + oxidized flavoprotein + H2O
-
 ?
demeclocycline + NADPH + H+ + O2
-
 Bacteroides thetaiotaomicron 11a-hydroxydemeclocycline + NADP+ + H2O
-
 ?
demeclocycline + reduced flavoprotein + O2
-
 Bacteroides fragilis 11a-hydroxy-demeclocycline + oxidized flavoprotein + H2O
-
 ?
doxycycline + NADPH + H+ + O2
-
 Bacteroides thetaiotaomicron 11a-hydroxydoxycycline + NADP+ + H2O
-
 ?
doxycycline + reduced flavoprotein + O2
-
 Bacteroides fragilis 11a-hydroxy-doxycycline + oxidized flavoprotein + H2O
-
 ?
minocycline + NADPH + H+ + O2
-
 Bacteroides thetaiotaomicron 11a-hydroxyminocycline + NADP+ + H2O
-
 ?
minocycline + reduced flavoprotein + O2
-
 Bacteroides fragilis 11a-hydroxy-minocycline + oxidized flavoprotein + H2O
-
 ?
additional information tetracycline substrates, initial monohydroxylation at position 11a followed by intramolecular cyclization and non-enzymatic breakdown to undefined products Bacteroides fragilis ?
-
 ?
additional information the enzyme shows a broad tetracycline antibiotic spectrum and a requirement for molecular oxygen and NADPH in antibiotic degradation. The tetracycline products are unstable at neutral pH, but mass spectral and NMR characterization under acidic conditions support initial monohydroxylation at position 11a followed by intramolecular cyclization and non-enzymatic breakdown to other undefined products Bacteroides thetaiotaomicron ?
-
 ?
oxytetracycline + reduced flavoprotein + NADPH + O2
-
 Bacteroides fragilis 11a-hydroxy-oxytetracycline + oxidized flavoprotein + H2O + NADP+
-
 ?
tetracycline + NADPH + H+ + O2
-
 Bacteroides thetaiotaomicron 11a-hydroxytetracycline + NADP+ + H2O
-
 ?
tetracycline + reduced flavoprotein + O2
-
 Bacteroides fragilis 11a-hydroxy-tetracycline + oxidized flavoprotein + H2O
-
 ?

Subunits

Subunits Comment Organism
monomer x * 44000, SDS-PAGE and deduced from gene sequence Bacteroides fragilis

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.12
-
 minocycline pH 8.5 Bacteroides fragilis
0.12
-
 minocycline pH 8.5, temperature not specified in the publication Bacteroides thetaiotaomicron
0.2
-
 demeclocycline pH 8.5 Bacteroides fragilis
0.2
-
 demeclocycline pH 8.5, temperature not specified in the publication Bacteroides thetaiotaomicron
0.3
-
 chlortetracycline pH 8.5 Bacteroides fragilis
0.3
-
 chlortetracycline pH 8.5, temperature not specified in the publication Bacteroides thetaiotaomicron
0.32
-
 tetracycline pH 8.5 Bacteroides fragilis
0.32
-
 tetracycline pH 8.5, temperature not specified in the publication Bacteroides thetaiotaomicron
0.63
-
 doxycycline pH 8.5 Bacteroides fragilis
0.63
-
 doxycycline pH 8.5, temperature not specified in the publication Bacteroides thetaiotaomicron
1.11
-
 NADPH pH 8.5 Bacteroides fragilis
1.11
-
 NADPH pH 8.5, temperature not specified in the publication Bacteroides thetaiotaomicron
1.3
-
 oxytetracycline pH 8.5 Bacteroides fragilis
1.3
-
 alpha-doxycycline pH 8.5, temperature not specified in the publication Bacteroides thetaiotaomicron

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
8.5
-
 assay at Bacteroides thetaiotaomicron

Cofactor

Cofactor Comment Organism Structure
FAD
-
 Bacteroides fragilis
NADPH
-
 Bacteroides fragilis

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
2.7
-
 chlortetracycline pH 8.5, temperature not specified in the publication Bacteroides thetaiotaomicron
4.1
-
 minocycline pH 8.5, temperature not specified in the publication Bacteroides thetaiotaomicron
5.9
-
 tetracycline pH 8.5, temperature not specified in the publication Bacteroides thetaiotaomicron
7.5
-
 doxycycline pH 8.5, temperature not specified in the publication Bacteroides thetaiotaomicron
8.3
-
 NADPH pH 8.5, temperature not specified in the publication Bacteroides thetaiotaomicron
10
-
 demeclocycline pH 8.5, temperature not specified in the publication Bacteroides thetaiotaomicron
17
-
 alpha-doxycycline pH 8.5, temperature not specified in the publication Bacteroides thetaiotaomicron