KEGG   ENZYME: 1.14.19.59Help
Entry
EC 1.14.19.59               Enzyme                                 

Name
tryptophan 6-halogenase;
sttH (gene name);
thdH (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 (6-halogenating)
Reaction(IUBMB)
(1) L-tryptophan + FADH2 + chloride + O2 + H+ = 6-chloro-L-tryptophan + FAD + 2 H2O [RN:R12032];
(2) D-tryptophan + FADH2 + chloride + O2 + H+ = 6-chloro-D-tryptophan + FAD + 2 H2O [RN:R12033]
Reaction(KEGG)
Substrate
L-tryptophan [CPD:C00078];
FADH2 [CPD:C01352];
chloride [CPD:C00698];
O2 [CPD:C00007];
H+ [CPD:C00080];
D-tryptophan [CPD:C00525]
Product
6-chloro-L-tryptophan [CPD:C21866];
FAD [CPD:C00016];
H2O [CPD:C00001];
6-chloro-D-tryptophan [CPD:C21867]
Comment
The enzyme is a flavin-dependent halogenase that has been described from several bacterial species. 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 1.14.19.58, tryptophan 5-halogenase, and EC 1.14.19.9, tryptophan 7-halogenase.
History
EC 1.14.19.59 created 2018
Orthology
K22694  tryptophan 6-halogenase
Genes
PTT: VY86_05165
MSD: MYSTI_03287 MYSTI_03293
DEQ: XM25_00370
MMI: MMAR_3632
MMAE: MMARE11_35390
MCHE: BB28_17530
MSTE: MSTE_03466
NSR: NS506_02367(prnA)
SHY: SHJG_8627
SHO: SHJGH_8387
SVE: SVEN_6229
STRE: GZL_02919
SRW: TUE45_00622(rebH_1) TUE45_06417(rebH_3)
SMAL: SMALA_6632
SALF: SMD44_02518(prnA) SMD44_06519(prnA)
SLX: SLAV_10460(rebH)
SFK: KY5_7454
SEN: SACE_4919(prnA)
AOI: AORI_5336(prnA)
SESP: BN6_32440(prnA) BN6_35860
KAL: KALB_5897
ACTI: UA75_17400
ACAD: UA74_16865
 » show all
Taxonomy
Reference
1  [PMID:21424165]
  Authors
Zeng J, Zhan J
  Title
Characterization of a tryptophan 6-halogenase from Streptomyces toxytricini.
  Journal
Biotechnol Lett 33:1607-13 (2011)
DOI:10.1007/s10529-011-0595-7
  Sequence
Reference
2  [PMID:24692213]
  Authors
Milbredt D, Patallo EP, van Pee KH
  Title
A tryptophan 6-halogenase and an amidotransferase are involved in thienodolin biosynthesis.
  Journal
Chembiochem 15:1011-20 (2014)
DOI:10.1002/cbic.201400016
  Sequence
Reference
3  [PMID:26840773]
  Authors
Shepherd SA, Menon BR, Fisk H, Struck AW, Levy C, Leys D, Micklefield J
  Title
A Structure-Guided Switch in the Regioselectivity of a Tryptophan Halogenase.
  Journal
Chembiochem 17:821-4 (2016)
DOI:10.1002/cbic.201600051
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.14.19.59
IUBMB Enzyme Nomenclature: 1.14.19.59
ExPASy - ENZYME nomenclature database: 1.14.19.59
BRENDA, the Enzyme Database: 1.14.19.59

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