KEGG   ORTHOLOGY: K14266
Entry
K14266                      KO                                     

Name
prnA, rebH, ktzQ
Definition
tryptophan 7-halogenase [EC:1.14.19.9]
Pathway
ko00404  Staurosporine biosynthesis
ko01100  Metabolic pathways
ko01110  Biosynthesis of secondary metabolites
Module
M00789  Rebeccamycin biosynthesis, tryptophan => rebeccamycin
M00790  Pyrrolnitrin biosynthesis, tryptophan => pyrrolnitrin
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00404 Staurosporine biosynthesis
    K14266  prnA, rebH, ktzQ; tryptophan 7-halogenase
Enzymes [BR:ko01000]
 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
    1.14.19.9  tryptophan 7-halogenase
     K14266  prnA, rebH, ktzQ; tryptophan 7-halogenase
Other DBs
RN: R09570
COG: COG0665
Genes
VUN: 114171700
LPV: HYN51_07845
IZH: FEM41_13305
SRR: SerAS9_4268
SRL: SOD_c40000
SRY: M621_21745
SPLY: Q5A_021600(prnA)
SRS: SerAS12_4269
SRA: SerAS13_4269
SMAF: D781_2597
XCC: XCC2825(prnA) XCC3966(prnA) XCC4133(prnA)
XAC: XAC2995(prnA) XAC4051(prnA) XAC4275(prnA)
XCI: XCAW_00251(prnA) XCAW_00399(prnA) XCAW_03274(prnA)
XOM: XOO0227(XOO0227) XOO0354(XOO0354) XOO1160(XOO1160)
XOO: XOO0248(prnA) XOO0391(prnA) XOO1263(prnA)
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
SSE: Ssed_1209
SPL: Spea_1098
SHL: Shal_1146
SPSW: Sps_02370
SKH: STH12_00467(rebH_1) STH12_01336(rebH_2) STH12_03665(rebH_3)
PHA: PSHAa1353
PTN: PTRA_a1709(prnA)
PTD: PTET_a1596(prnA) PTET_a2158(prnA)
PSEN: PNC201_06690(rebH1)
MICC: AUP74_00047(rebH_2) AUP74_00418(rebH_3) AUP74_01694(rebH_5) AUP74_01714(rebH_6) AUP74_01717(rebH_7)
MICT: FIU95_18620(prnA)
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
MEX: Mext_2404
MPO: Mpop_2363
META: Y590_11615
PZU: PHZ_c2922
SPHP: LH20_00455
ELI: ELI_03165
ERF: FIU90_07215(prnA1) FIU90_07230(rebH1) FIU90_14280(rebH2) FIU90_14285(rebH3) FIU90_14290(rebH4) FIU90_14295(rebH5) FIU90_15030(prnA2)
AAY: WYH_02200(rebH)
ANH: A6F65_00847(rebH_2) A6F65_02486(prnA)
ADO: A6F68_02840(rebH) A6F68_02902(prnA)
BBA: Bd1390(prnA)
BBAT: Bdt_1370(prnA)
BBAC: EP01_16870
SRW: TUE45_04027(rebH_2)
FMR: Fuma_01240(rebH_1) Fuma_01246(rebH_2)
SALI: L593_06180
AG: AAB97504(prnA) ABV56597(ktzQ) BAC10682(rebH)
 » show all
Reference
PMID:9172332
  Authors
Hammer PE, Hill DS, Lam ST, Van Pee KH, Ligon JM
  Title
Four genes from Pseudomonas fluorescens that encode the biosynthesis of pyrrolnitrin.
  Journal
Appl Environ Microbiol 63:2147-54 (1997)
DOI:10.1128/AEM.63.6.2147-2154.1997
  Sequence
Reference
  Authors
Keller S, Wage T, Hohaus K, Holzer M, Eichhorn E, van Pee KH
  Title
Purification and Partial Characterization of Tryptophan 7-Halogenase (PrnA) from Pseudomonas fluorescens.
  Journal
Angew Chem Int Ed Engl 39:2300-2302 (2000)
DOI:10.1002/1521-3773(20000703)39:13<2300::AID-ANIE2300>3.0.CO;2-I
Reference
  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
  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

KEGG   ENZYME: 1.14.19.9
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
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)
R09570
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
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K14266  tryptophan 7-halogenase
Genes
VUN: 114171700
LPV: HYN51_07845
IZH: FEM41_13305
SRR: SerAS9_4268
SRL: SOD_c40000
SRY: M621_21745
SPLY: Q5A_021600(prnA)
SRS: SerAS12_4269
SRA: SerAS13_4269
SMAF: D781_2597
XCC: XCC2825(prnA) XCC3966(prnA) XCC4133(prnA)
XAC: XAC2995(prnA) XAC4051(prnA) XAC4275(prnA)
XCI: XCAW_00251(prnA) XCAW_00399(prnA) XCAW_03274(prnA)
XOM: XOO0227(XOO0227) XOO0354(XOO0354) XOO1160(XOO1160)
XOO: XOO0248(prnA) XOO0391(prnA) XOO1263(prnA)
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
SSE: Ssed_1209
SPL: Spea_1098
SHL: Shal_1146
SPSW: Sps_02370
SKH: STH12_00467(rebH_1) STH12_01336(rebH_2) STH12_03665(rebH_3)
PHA: PSHAa1353
PTN: PTRA_a1709(prnA)
PTD: PTET_a1596(prnA) PTET_a2158(prnA)
PSEN: PNC201_06690(rebH1)
MICC: AUP74_00047(rebH_2) AUP74_00418(rebH_3) AUP74_01694(rebH_5) AUP74_01714(rebH_6) AUP74_01717(rebH_7)
MICT: FIU95_18620(prnA)
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
MEX: Mext_2404
MPO: Mpop_2363
META: Y590_11615
PZU: PHZ_c2922
SPHP: LH20_00455
ELI: ELI_03165
ERF: FIU90_07215(prnA1) FIU90_07230(rebH1) FIU90_14280(rebH2) FIU90_14285(rebH3) FIU90_14290(rebH4) FIU90_14295(rebH5) FIU90_15030(prnA2)
AAY: WYH_02200(rebH)
ANH: A6F65_00847(rebH_2) A6F65_02486(prnA)
ADO: A6F68_02840(rebH) A6F68_02902(prnA)
BBA: Bd1390(prnA)
BBAT: Bdt_1370(prnA)
BBAC: EP01_16870
SRW: TUE45_04027(rebH_2)
FMR: Fuma_01240(rebH_1) Fuma_01246(rebH_2)
SALI: L593_06180
 » show all
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

KEGG   REACTION: R09570
Entry
R09570                      Reaction                               

Name
L-tryptophan:FADH2 oxidoreductase (7-halogenating)
Definition
L-Tryptophan + FADH2 + Cl- + Oxygen + H+ <=> 7-Chloro-L-tryptophan + FAD + 2 H2O
Equation
Reaction class
RC00126  C00016_C01352
RC00949  C00078_C19687
Enzyme
Pathway
rn00404  Staurosporine biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00789  Rebeccamycin biosynthesis, tryptophan => rebeccamycin
M00790  Pyrrolnitrin biosynthesis, tryptophan => pyrrolnitrin
Orthology
K14266  tryptophan 7-halogenase [EC:1.14.19.9]
Other DBs
RHEA: 26497

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