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

BRENDA support

Literature summary for 1.14.19.9 extracted from

  • Yeh, E.; Garneau, S.; Walsh, C.T.
    Robust in vitro activity of RebF and RebH, a two-component reductase/halogenase, generating 7-chlorotryptophan during rebeccamycin biosynthesis (2005), Proc. Natl. Acad. Sci. USA, 102, 3960-3965.
    View publication on PubMedView publication on EuropePMC
Search for more literature for 1.14.19.9

Protein Variants

Protein Variants Comment Organism
additional information gene disruption mutant, no production of pyrroindomycin B, but still production of pyrroindomycin A Lentzea aerocolonigenes

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.002
-
 L-tryptophan pH 7.5 Lentzea aerocolonigenes

Organism

Organism UniProt Comment Textmining
Lentzea aerocolonigenes Q8KHZ8 Halogenation requires the presence of RebF, which catalyzes the NADH-dependent reduction of FAD to provide FADH2 for the halogenase
-
Lentzea aerocolonigenes 39243 Q8KHZ8 Halogenation requires the presence of RebF, which catalyzes the NADH-dependent reduction of FAD to provide FADH2 for the halogenase
-

Purification (Commentary)

Purification (Comment) Organism
recombinant enzyme Lentzea aerocolonigenes

Reaction

Reaction Comment Organism Reaction ID
tryptophan + FADH2 + chloride + O2 + H+ = 7-chloro-L-tryptophan + FAD + 2 H2O proposed mechanism: after formation of a FAD-OOH intermediate, the reactive chlorine is generated as a FAD-O-Cl intermediate. Chlorination of L-tryptophan proceeds by attack of the aromatic pi electrons on the intermediate in a two-electron mechanism and abstraction of a proton generates the final product Lentzea aerocolonigenes
a

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
L-tryptophan + FADH2 + Br- + O2 + H+
-
 Lentzea aerocolonigenes 7-bromo-L-tryptophan + FAD + H2O identity of product is confirmed by ESI-MS and 1H-NMR. Reaction is selective for the 7-position. Brominating activity is about 75% of chlorinating activity ?
L-tryptophan + FADH2 + Br- + O2 + H+
-
 Lentzea aerocolonigenes 39243 7-bromo-L-tryptophan + FAD + H2O identity of product is confirmed by ESI-MS and 1H-NMR. Reaction is selective for the 7-position. Brominating activity is about 75% of chlorinating activity ?
L-tryptophan + FADH2 + Cl- + O2 + H+
-
 Lentzea aerocolonigenes 7-chloro-L-tryptophan + FAD + H2O identity of product is confirmed by ESI-MS and 1H-NMR ?
L-tryptophan + FADH2 + Cl- + O2 + H+
-
 Lentzea aerocolonigenes 39243 7-chloro-L-tryptophan + FAD + H2O identity of product is confirmed by ESI-MS and 1H-NMR ?
additional information O2 and presence of RebF, which catalyzes the NADH-dependent reduction of FAD to provide FADH2 for the halogenase, are required for reaction. 54% of available L-tryptophan are converted within 5 min when the reaction is prepapred anaerobically and O2 is introduced slowly. Reaction rate drops by 90% in air-saturated conditions. No substrate: fluoride, iodide Lentzea aerocolonigenes ?
-
 ?
additional information O2 and presence of RebF, which catalyzes the NADH-dependent reduction of FAD to provide FADH2 for the halogenase, are required for reaction. 54% of available L-tryptophan are converted within 5 min when the reaction is prepapred anaerobically and O2 is introduced slowly. Reaction rate drops by 90% in air-saturated conditions. No substrate: fluoride, iodide Lentzea aerocolonigenes 39243 ?
-
 ?

Synonyms

Synonyms Comment Organism
RebH
-
 Lentzea aerocolonigenes

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.023
-
 L-tryptophan pH 7.5 Lentzea aerocolonigenes

Cofactor

Cofactor Comment Organism Structure
FADH2
-
 Lentzea aerocolonigenes
additional information no cofactor: NADPH, FMN Lentzea aerocolonigenes