KEGG   ENZYME: 1.14.19.58Help
Entry
EC 1.14.19.58               Enzyme                                 

Name
tryptophan 5-halogenase;
pyrH (gene name)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With oxidation of a pair of donors resulting in the reduction of O2 to two molecules of water
BRITE hierarchy
Sysname
L-tryptophan:FADH2 oxidoreductase (5-halogenating)
Reaction(IUBMB)
L-tryptophan + FADH2 + chloride + O2 + H+ = 5-chloro-L-tryptophan + FAD + 2 H2O [RN:R12031]
Reaction(KEGG)
Substrate
L-tryptophan [CPD:C00078];
FADH2 [CPD:C01352];
chloride [CPD:C00698];
O2 [CPD:C00007];
H+ [CPD:C00080]
Product
5-chloro-L-tryptophan [CPD:C21865];
FAD [CPD:C00016];
H2O [CPD:C00001]
Comment
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.
History
EC 1.14.19.58 created 2018
Orthology
K22693  tryptophan 5-halogenase
Genes
SGV: B1H19_08825
PSEQ: AD006_32380
KAL: KALB_6284
Taxonomy
Reference
1  [PMID:15850981]
  Authors
Zehner S, Kotzsch A, Bister B, Sussmuth RD, Mendez C, Salas JA, van Pee KH
  Title
A regioselective tryptophan 5-halogenase is involved in pyrroindomycin biosynthesis in Streptomyces rugosporus LL-42D005.
  Journal
Chem Biol 12:445-52 (2005)
DOI:10.1016/j.chembiol.2005.02.005
  Sequence
Reference
2  [PMID:19501593]
  Authors
Zhu X, De Laurentis W, Leang K, Herrmann J, Ihlefeld K, van Pee KH, Naismith JH
  Title
Structural insights into regioselectivity in the enzymatic chlorination of tryptophan.
  Journal
J Mol Biol 391:74-85 (2009)
DOI:10.1016/j.jmb.2009.06.008
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.14.19.58
IUBMB Enzyme Nomenclature: 1.14.19.58
ExPASy - ENZYME nomenclature database: 1.14.19.58
BRENDA, the Enzyme Database: 1.14.19.58

DBGET integrated database retrieval system