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2aqj

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[[Image:2aqj.gif|left|200px]]<br /><applet load="2aqj" size="350" color="white" frame="true" align="right" spinBox="true"
 
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caption="2aqj, resolution 1.800&Aring;" />
 
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'''The structure of tryptophan 7-halogenase (PrnA) suggests a mechanism for regioselective chlorination'''<br />
 
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==Overview==
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==The structure of tryptophan 7-halogenase (PrnA) suggests a mechanism for regioselective chlorination==
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Chlorinated natural products include vancomycin and cryptophycin A. Their biosynthesis involves regioselective chlorination by flavin-dependent halogenases. We report the structural characterization of tryptophan 7-halogenase (PrnA), which regioselectively chlorinates tryptophan. Tryptophan and flavin adenine dinucleotide (FAD) are separated by a 10 angstrom-long tunnel and bound by distinct enzyme modules. The FAD module is conserved in halogenases and is related to flavin-dependent monooxygenases. On the basis of biochemical studies, crystal structures, and by analogy with monooxygenases, we predict that FADH2 reacts with O2 to make peroxyflavin, which is decomposed by Cl-. The resulting HOCl is guided through the tunnel to tryptophan, where it is activated to participate in electrophilic aromatic substitution.
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<StructureSection load='2aqj' size='340' side='right'caption='[[2aqj]], [[Resolution|resolution]] 1.80&Aring;' scene=''>
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== Structural highlights ==
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==About this Structure==
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<table><tr><td colspan='2'>[[2aqj]] is a 1 chain structure with sequence from [https://en.wikipedia.org/wiki/Pseudomonas_fluorescens Pseudomonas fluorescens]. Full crystallographic information is available from [http://oca.weizmann.ac.il/oca-bin/ocashort?id=2AQJ OCA]. For a <b>guided tour on the structure components</b> use [https://proteopedia.org/fgij/fg.htm?mol=2AQJ FirstGlance]. <br>
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2AQJ is a [http://en.wikipedia.org/wiki/Single_protein Single protein] structure of sequence from [http://en.wikipedia.org/wiki/Pseudomonas_fluorescens Pseudomonas fluorescens] with <scene name='pdbligand=CL:'>CL</scene>, <scene name='pdbligand=TRP:'>TRP</scene> and <scene name='pdbligand=FAD:'>FAD</scene> as [http://en.wikipedia.org/wiki/ligands ligands]. Full crystallographic information is available from [http://oca.weizmann.ac.il/oca-bin/ocashort?id=2AQJ OCA].
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</td></tr><tr id='method'><td class="sblockLbl"><b>[[Empirical_models|Method:]]</b></td><td class="sblockDat" id="methodDat">X-ray diffraction, [[Resolution|Resolution]] 1.8&#8491;</td></tr>
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<tr id='ligand'><td class="sblockLbl"><b>[[Ligand|Ligands:]]</b></td><td class="sblockDat" id="ligandDat"><scene name='pdbligand=CL:CHLORIDE+ION'>CL</scene>, <scene name='pdbligand=FAD:FLAVIN-ADENINE+DINUCLEOTIDE'>FAD</scene>, <scene name='pdbligand=TRP:TRYPTOPHAN'>TRP</scene></td></tr>
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==Reference==
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<tr id='resources'><td class="sblockLbl"><b>Resources:</b></td><td class="sblockDat"><span class='plainlinks'>[https://proteopedia.org/fgij/fg.htm?mol=2aqj FirstGlance], [http://oca.weizmann.ac.il/oca-bin/ocaids?id=2aqj OCA], [https://pdbe.org/2aqj PDBe], [https://www.rcsb.org/pdb/explore.do?structureId=2aqj RCSB], [https://www.ebi.ac.uk/pdbsum/2aqj PDBsum], [https://prosat.h-its.org/prosat/prosatexe?pdbcode=2aqj ProSAT]</span></td></tr>
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Tryptophan 7-halogenase (PrnA) structure suggests a mechanism for regioselective chlorination., Dong C, Flecks S, Unversucht S, Haupt C, van Pee KH, Naismith JH, Science. 2005 Sep 30;309(5744):2216-9. PMID:[http://ispc.weizmann.ac.il//pmbin/getpm?pmid=16195462 16195462]
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</table>
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== Function ==
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[https://www.uniprot.org/uniprot/PRNA_PSEFL PRNA_PSEFL] Involved in the biosynthesis of the antifungal antibiotic pyrrolnitrin. Catalyze the chlorination of tryptophan (Trp) at C7 position to yield 7-chloro-L-tryptophan (7-CLT). The reaction between FADH2, Cl-, and O2 generates the powerful oxidant HOCl, which is presumed to carry out the chlorination reaction. The reaction of HOCl with the active site Lys-79 generates a lysine chloramine, which plays a key role in directing regiospecific chlorination of substrate in this important class of biosynthetic enzymes. It is also able to use bromide ions to generate monobrominated Trp.<ref>PMID:10941070</ref> <ref>PMID:9172332</ref> <ref>PMID:9537395</ref>
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== Evolutionary Conservation ==
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[[Image:Consurf_key_small.gif|200px|right]]
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Check<jmol>
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<jmolCheckbox>
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<scriptWhenChecked>; select protein; define ~consurf_to_do selected; consurf_initial_scene = true; script "/wiki/ConSurf/aq/2aqj_consurf.spt"</scriptWhenChecked>
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<scriptWhenUnchecked>script /wiki/extensions/Proteopedia/spt/initialview01.spt</scriptWhenUnchecked>
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<text>to colour the structure by Evolutionary Conservation</text>
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</jmolCheckbox>
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</jmol>, as determined by [http://consurfdb.tau.ac.il/ ConSurfDB]. You may read the [[Conservation%2C_Evolutionary|explanation]] of the method and the full data available from [http://bental.tau.ac.il/new_ConSurfDB/main_output.php?pdb_ID=2aqj ConSurf].
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<div style="clear:both"></div>
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== References ==
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<references/>
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__TOC__
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</StructureSection>
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[[Category: Large Structures]]
[[Category: Pseudomonas fluorescens]]
[[Category: Pseudomonas fluorescens]]
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[[Category: Single protein]]
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[[Category: Dong C]]
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[[Category: Dong, C.]]
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[[Category: Flecks S]]
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[[Category: Flecks, S.]]
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[[Category: Haupt C]]
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[[Category: Haupt, C.]]
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[[Category: Naismith JH]]
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[[Category: Naismith, J H.]]
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[[Category: Unversucht S]]
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[[Category: Pee, K H.Van.]]
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[[Category: Van Pee K-H]]
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[[Category: SSPF, Scottish Structural Proteomics Facility.]]
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[[Category: Unversucht, S.]]
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[[Category: CL]]
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[[Category: FAD]]
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[[Category: TRP]]
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[[Category: flavin-dependent halogenase]]
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[[Category: helical bundle]]
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[[Category: sandwiched sheets]]
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[[Category: scottish structural proteomics facility]]
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[[Category: sspf]]
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[[Category: structural genomics]]
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[[Category: tryptophan 7-halogenase]]
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''Page seeded by [http://oca.weizmann.ac.il/oca OCA ] on Thu Feb 21 16:29:50 2008''
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Current revision

The structure of tryptophan 7-halogenase (PrnA) suggests a mechanism for regioselective chlorination

PDB ID 2aqj

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