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1.14.19.58: tryptophan 5-halogenase

This is an abbreviated version!
For detailed information about tryptophan 5-halogenase, go to the full flat file.

Word Map on EC 1.14.19.58

Reaction

L-tryptophan
+
FADH2
 +
chloride
 +
O2
 +
H+
=
5-chloro-L-tryptophan
 +
FAD
 + 2 H2O

Synonyms

halogenase, mibH, pyrH, sttH, trp-5-halogenase

ECTree

     1 Oxidoreductases
         1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
             1.14.19 With oxidation of a pair of donors resulting in the reduction of O2 to two molecules of water
                1.14.19.58 tryptophan 5-halogenase

Systematic Name

Systematic Name on EC 1.14.19.58 - tryptophan 5-halogenase

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SYSTEMATIC NAME
IUBMB Comments
L-tryptophan:FADH2 oxidoreductase (5-halogenating)
A flavin-dependent halogenase. The enzyme from the bacterium Streptomyces rugosporus catalyses halogenation of the C-5 position of tryptophan during the biosynthesis of the antibiotic compound pyrroindomycin B. It utilizes molecular oxygen to oxidize the FADH2 cofactor, giving C4a-hydroperoxyflavin, which then reacts with chloride to produce a hypochlorite ion. The latter reacts with an active site lysine to generate a chloramine, which chlorinates the substrate. cf. EC 1.14.19.59, tryptophan 6-halogenase and EC 1.14.19.9, tryptophan 7-halogenase.