KEGG ENZYME: 1.14.19.59

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

DRP:	PSQ90_11805

SSTL:

ABFK29_19810

NSM:	JO391_13500

MSD:	MYSTI_03287 MYSTI_03293

MLAN:

JY572_10190 JY572_10220

MMI:

MMAR_3632

MMAE:

MMARE11_35390

MPSE:

MPSD_36980

MSHO:

MSHO_33320

MCHE:

BB28_17530

MSTE:

MSTE_03466

MSAL:

DSM43276_03250(rebH)

NSR:	NS506_02367(prnA)

SHY:

SHJG_8627

SHO:	SHJGH_8387

SMAL:

SMALA_6632

SSOI:

I1A49_36935

SVE:

SVEN_6229

SCI:	B446_23735

SGU:	SGLAU_04505

STRE:

GZL_02919

SRW:	TUE45_00622(rebH_1) TUE45_06417(rebH_3)

STSI:

A4E84_32635

SCAD:

DN051_13765

SNR:	SNOUR_12610

SSIA:

A7J05_33480

SPUN:

BFF78_15620

SALF:

SMD44_02518(prnA)

SLX:	SLAV_10460(rebH)

SFK:

KY5_7454

SLK:	SLUN_13725

SKA:	CP970_02920

SVN:	CP980_28410

SPAD:

DVK44_09645

SRIM:

CP984_09605

SSUB:

CP968_16685 CP968_32180

SNF:	JYK04_01552(rebH)

SHUN:

DWB77_02862(rebH)

SLIA:

HA039_20560

SDD:	D9753_04005

SAOV:

G3H79_23745

SYAN:

NRK68_04395

STUB:

MMF93_00095

SYUN:

MOV08_12420

SOV:	QZH56_21225

STTN:

BSL84_04140

STPB:

QR97_23410 QR97_37415

SMIB:

SMIR_00255

STRL:

HEP84_44365

STSD:

HEP87_45495

SCHE:

QRN89_03805

SGLY:

P8A20_25375

KCH:	O1G21_36980

STRH:

GXP74_21295

NFE:	HUT17_05350

SEN:	SACE_4919(prnA)

AOI:	AORI_5336(prnA)

AMYZ:

HUW46_07940(rebH_1) HUW46_09459(rebH_2)

SESP:

BN6_32440(prnA) BN6_35860

SACX:

IOD16_11965

KAL:

KALB_5897

KUT:	JJ691_19070 JJ691_20610

LED:	BBK82_44290

ACTI:

UA75_17400

ACAD:

UA74_16865

ACTA:

C1701_15530 C1701_26640

MFEU:

H1D33_25010

DVC:	Dvina_05900 Dvina_38565

DMAT:

Dmats_05380 Dmats_33520

NLK:	NIES25_46520

NCW:	NIES2107_04390

HBQ:	QI031_11935

KBS:	EPA93_03080

HNO:	LT974_07900

HAXY:

NGM07_12070

» 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

[ag:ADW94630]

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

[ag:AGF50179]

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

[ag:ADW94630]

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

All links

Chemical substance (10)   
   KEGG COMPOUND (10)   
Chemical reaction (3)   
   KEGG REACTION (2)   
   KEGG RCLASS (1)   
Gene (110)   
   KEGG ORTHOLOGY (1)   
   KEGG GENES (88)   
   KEGG MGENES (21)   
Protein sequence (4)   
   UniProt (2)   
   SWISS-PROT (2)   
DNA sequence (1)   
   GenBank (1)   
Protein domain (4)   
   InterPro (4)   
All databases (132)   

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