KEGG   ENZYME: 1.14.19.59
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
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)
R12032 R12033
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
MSDMYSTI_03287 MYSTI_03293
NSMJO391_13500
SNEANBZ79_10035
MMIMMAR_3632
MMAEMMARE11_35390
MPSEMPSD_36980
MSHOMSHO_33320
MCHEBB28_17530
MSTEMSTE_03466
MSALDSM43276_03250(rebH)
NSRNS506_02367(prnA)
SHYSHJG_8627
SHOSHJGH_8387
SMALSMALA_6632
SSOII1A49_36935
SVESVEN_6229
SCIB446_23735
SGUSGLAU_04505
STREGZL_02919
SRWTUE45_00622(rebH_1) TUE45_06417(rebH_3)
STSIA4E84_32635
SCADDN051_13765
SNRSNOUR_12610
SSIAA7J05_33480
SPUNBFF78_15620
SALFSMD44_02518(prnA)
SLXSLAV_10460(rebH)
SFKKY5_7454
SLKSLUN_13725
SKACP970_02920
SVNCP980_28410
SPADDVK44_09645
SRIMCP984_09605
SSUBCP968_16685 CP968_32180
SNFJYK04_01552(rebH)
SHUNDWB77_02862(rebH)
SLIAHA039_20560
SDDD9753_04005
NFEHUT17_05350
SENSACE_4919(prnA)
AOIAORI_5336(prnA)
SESPBN6_32440(prnA) BN6_35860
KALKALB_5897
LEDBBK82_44290
ACTIUA75_17400
ACADUA74_16865
ACTAC1701_15530 C1701_26640
DVCDvina_05900 Dvina_38565
KBSEPA93_03080
HNOLT974_07900
 » show all
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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