KEGG   ENZYME: 1.14.19.9Help
Entry
EC 1.14.19.9                Enzyme                                 

Name
tryptophan 7-halogenase;
prnA (gene name);
rebH (gene name);
ktzQ (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 (7-halogenating)
Reaction(IUBMB)
tryptophan + FADH2 + chloride + O2 + H+ = 7-chloro-L-tryptophan + FAD + 2 H2O [RN:R09570]
Reaction(KEGG)
Substrate
tryptophan [CPD:C00078];
FADH2 [CPD:C01352];
chloride [CPD:C00698];
O2 [CPD:C00007];
H+ [CPD:C00080]
Product
7-chloro-L-tryptophan [CPD:C19687];
FAD [CPD:C00016];
H2O [CPD:C00001]
Comment
A flavin-dependent halogenase. The enzyme from the bacterium Lechevalieria aerocolonigenes catalyses the initial step in the biosynthesis of rebeccamycin [2]. 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. Also acts on bromide ion. cf. EC 1.14.19.58, tryptophan 5-halogenase, and EC 1.14.19.59, tryptophan 6-halogenase.
History
EC 1.14.19.9 created 2009 as EC 1.14.14.7, transferred 2014 to EC 1.14.19.9, modified 2018
Pathway
ec00404  Staurosporine biosynthesis
ec01130  Biosynthesis of antibiotics
Orthology
K14266  tryptophan 7-halogenase
Genes
LPV: HYN51_07845
SRR: SerAS9_4268
SRL: SOD_c40000
SRY: M621_21745
SPLY: Q5A_021600(prnA)
SRS: SerAS12_4269
SRA: SerAS13_4269
SMAF: D781_2597
SRZ: AXX16_2520
SERM: CLM71_13470
XCC: XCC2825(prnA) XCC3966(prnA) XCC4133(prnA)
XAC: XAC2995(prnA) XAC4051(prnA) XAC4275(prnA)
XCI: XCAW_00251(prnA) XCAW_00399(prnA) XCAW_03274(prnA)
XOO: XOO0248(prnA) XOO0391(prnA) XOO1263(prnA)
XOM: XOO0227(XOO0227) XOO0354(XOO0354) XOO1160(XOO1160)
XPH: XppCFBP6546_12895(XppCFBP6546P_12895) XppCFBP6546_14225(XppCFBP6546P_14225) XppCFBP6546_20780(XppCFBP6546P_20780)
SMZ: SMD_2241
PSD: DSC_13765
PFL: PFL_3604(prnA)
PPRO: PPC_3743(prnA)
PSEM: TO66_16635
SON: SO_3513
SAZ: Sama_0939
SBL: Sbal_1121
SSE: Ssed_1209
SPL: Spea_1098
SHL: Shal_1146
SWP: swp_1626
PHA: PSHAa1353
PTN: PTRA_a1709(prnA)
PEA: PESP_a1684(prnA) PESP_a2173(prnA) PESP_a2210(prnA) PESP_a2309(prnA)
PART: PARC_a1605(prnA) PARC_a2299(prnA)
PTU: PTUN_a1620(prnA) PTUN_a1726 PTUN_a1728(prnA) PTUN_a1858(prnA)
PNG: PNIG_a1798(prnA)
PTD: PTET_a1596(prnA) PTET_a2158(prnA)
PSEN: PNC201_06690(rebH1)
AMAL: I607_09170
AMAE: I876_09530
AMAO: I634_09610
AMAG: I533_09490
GNI: GNIT_3223
MICC: AUP74_00047(rebH_2) AUP74_00418(rebH_3) AUP74_01717(rebH_7)
BPM: BURPS1710b_A1115(prnA)
BPSE: BDL_5422(prnA)
BPSM: BBQ_4121(prnA)
BPSU: BBN_5475(prnA)
BPSD: BBX_4589(prnA)
BPK: BBK_4751(prnA)
BPSH: DR55_5722(prnA)
BPSA: BBU_3999(prnA)
BPSO: X996_5526(prnA)
BUT: X994_5084(prnA)
BTZ: BTL_5470(prnA)
BTHA: DR62_5270
BOK: DM82_6302(prnA)
BAM: Bamb_4726
BCON: NL30_32800
BUB: BW23_5778(prnA)
BSEM: WJ12_18250
BMEC: WJ16_17180
RFR: Rfer_1114
LIM: L103DPR2_00071(prnA)
LCH: Lcho_3228
BBA: Bd1390(prnA)
BBAT: Bdt_1370(prnA)
BBAC: EP01_16870
MEX: Mext_2404
MPO: Mpop_2363
META: Y590_11615
PZU: PHZ_c2922
SPHP: LH20_00455
SMAZ: LH19_14975
SSAN: NX02_18010
SPHR: BSY17_3569
ELI: ELI_03165
ANH: A6F65_00847(rebH_2) A6F65_02486(prnA)
ADO: A6F68_02902(prnA)
SRW: TUE45_04027(rebH_2)
FMR: Fuma_01240(rebH_1) Fuma_01246(rebH_2)
SALI: L593_06180
 » show all
Taxonomy
Reference
1  [PMID:15272170]
  Authors
Dong C, Kotzsch A, Dorward M, van Pee KH, Naismith JH
  Title
Crystallization and X-ray diffraction of a halogenating enzyme, tryptophan 7-halogenase, from Pseudomonas fluorescens.
  Journal
Acta Crystallogr D Biol Crystallogr 60:1438-40 (2004)
DOI:10.1107/S0907444904012521
  Sequence
Reference
2  [PMID:15743914]
  Authors
Yeh E, Garneau S, Walsh CT
  Title
Robust in vitro activity of RebF and RebH, a two-component reductase/halogenase,  generating 7-chlorotryptophan during rebeccamycin biosynthesis.
  Journal
Proc Natl Acad Sci U S A 102:3960-5 (2005)
DOI:10.1073/pnas.0500755102
  Sequence
Reference
3  [PMID:17876823]
  Authors
Bitto E, Huang Y, Bingman CA, Singh S, Thorson JS, Phillips GN Jr
  Title
The structure of flavin-dependent tryptophan 7-halogenase RebH.
  Journal
Proteins 70:289-93 (2008)
DOI:10.1002/prot.21627
  Sequence
Reference
4  [PMID:18828589]
  Authors
Heemstra JR Jr, Walsh CT
  Title
Tandem action of the O2- and FADH2-dependent halogenases KtzQ and KtzR produce 6,7-dichlorotryptophan for kutzneride assembly.
  Journal
J Am Chem Soc 130:14024-5 (2008)
DOI:10.1021/ja806467a
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.14.19.9
IUBMB Enzyme Nomenclature: 1.14.19.9
ExPASy - ENZYME nomenclature database: 1.14.19.9
BRENDA, the Enzyme Database: 1.14.19.9

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