1u0w

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(New page: 200px<br /><applet load="1u0w" size="450" color="white" frame="true" align="right" spinBox="true" caption="1u0w, resolution 2.00&Aring;" /> '''An Aldol Switch Disc...)
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[[Image:1u0w.gif|left|200px]]<br /><applet load="1u0w" size="450" color="white" frame="true" align="right" spinBox="true"
 
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caption="1u0w, resolution 2.00&Aring;" />
 
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'''An Aldol Switch Discovered in Stilbene Synthases Mediates Cyclization Specificity of Type III Polyketide Synthases: 18xCHS+resveratrol Structure'''<br />
 
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==Overview==
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==An Aldol Switch Discovered in Stilbene Synthases Mediates Cyclization Specificity of Type III Polyketide Synthases: 18xCHS+resveratrol Structure==
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Stilbene synthase (STS) and chalcone synthase (CHS) each catalyze the, formation of a tetraketide intermediate from a CoA-tethered, phenylpropanoid starter and three molecules of malonyl-CoA, but use, different cyclization mechanisms to produce distinct chemical scaffolds, for a variety of plant natural products. Here we present the first STS, crystal structure and identify, by mutagenic conversion of alfalfa CHS, into a functional stilbene synthase, the structural basis for the, evolution of STS cyclization specificity in type III polyketide synthase, (PKS) enzymes. Additional mutagenesis and enzymatic characterization, confirms that electronic effects rather than steric factors balance, competing cyclization specificities in CHS and STS. Finally, we discuss, the problematic in vitro reconstitution of plant stilbenecarboxylate, pathways, using insights from existing biomimetic polyketide cyclization, studies to generate a novel mechanistic hypothesis to explain, stilbenecarboxylate biosynthesis.
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<StructureSection load='1u0w' size='340' side='right'caption='[[1u0w]], [[Resolution|resolution]] 2.00&Aring;' scene=''>
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== Structural highlights ==
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<table><tr><td colspan='2'>[[1u0w]] is a 4 chain structure with sequence from [https://en.wikipedia.org/wiki/Medicago_sativa Medicago sativa]. Full crystallographic information is available from [http://oca.weizmann.ac.il/oca-bin/ocashort?id=1U0W OCA]. For a <b>guided tour on the structure components</b> use [https://proteopedia.org/fgij/fg.htm?mol=1U0W FirstGlance]. <br>
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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]] 2&#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=STL:RESVERATROL'>STL</scene></td></tr>
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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=1u0w FirstGlance], [http://oca.weizmann.ac.il/oca-bin/ocaids?id=1u0w OCA], [https://pdbe.org/1u0w PDBe], [https://www.rcsb.org/pdb/explore.do?structureId=1u0w RCSB], [https://www.ebi.ac.uk/pdbsum/1u0w PDBsum], [https://prosat.h-its.org/prosat/prosatexe?pdbcode=1u0w ProSAT]</span></td></tr>
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</table>
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== Function ==
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[https://www.uniprot.org/uniprot/CHS2_MEDSA CHS2_MEDSA] The primary product of this enzyme is 4,2',4',6'-tetrahydroxychalcone (also termed naringenin-chalcone or chalcone) which can under specific conditions spontaneously isomerize into naringenin.<ref>PMID:10653632</ref> <ref>PMID:11732902</ref> <ref>PMID:11959984</ref> <ref>PMID:15380179</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/u0/1u0w_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=1u0w ConSurf].
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<div style="clear:both"></div>
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<div style="background-color:#fffaf0;">
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== Publication Abstract from PubMed ==
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Stilbene synthase (STS) and chalcone synthase (CHS) each catalyze the formation of a tetraketide intermediate from a CoA-tethered phenylpropanoid starter and three molecules of malonyl-CoA, but use different cyclization mechanisms to produce distinct chemical scaffolds for a variety of plant natural products. Here we present the first STS crystal structure and identify, by mutagenic conversion of alfalfa CHS into a functional stilbene synthase, the structural basis for the evolution of STS cyclization specificity in type III polyketide synthase (PKS) enzymes. Additional mutagenesis and enzymatic characterization confirms that electronic effects rather than steric factors balance competing cyclization specificities in CHS and STS. Finally, we discuss the problematic in vitro reconstitution of plant stilbenecarboxylate pathways, using insights from existing biomimetic polyketide cyclization studies to generate a novel mechanistic hypothesis to explain stilbenecarboxylate biosynthesis.
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==About this Structure==
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An aldol switch discovered in stilbene synthases mediates cyclization specificity of type III polyketide synthases.,Austin MB, Bowman ME, Ferrer JL, Schroder J, Noel JP Chem Biol. 2004 Sep;11(9):1179-94. PMID:15380179<ref>PMID:15380179</ref>
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1U0W is a [http://en.wikipedia.org/wiki/Single_protein Single protein] structure of sequence from [http://en.wikipedia.org/wiki/Medicago_sativa Medicago sativa] with STL as [http://en.wikipedia.org/wiki/ligand ligand]. Active as [http://en.wikipedia.org/wiki/Naringenin-chalcone_synthase Naringenin-chalcone synthase], with EC number [http://www.brenda-enzymes.info/php/result_flat.php4?ecno=2.3.1.74 2.3.1.74] Full crystallographic information is available from [http://ispc.weizmann.ac.il/oca-bin/ocashort?id=1U0W OCA].
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==Reference==
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From MEDLINE&reg;/PubMed&reg;, a database of the U.S. National Library of Medicine.<br>
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An aldol switch discovered in stilbene synthases mediates cyclization specificity of type III polyketide synthases., Austin MB, Bowman ME, Ferrer JL, Schroder J, Noel JP, Chem Biol. 2004 Sep;11(9):1179-94. PMID:[http://ispc.weizmann.ac.il//pmbin/getpm?pmid=15380179 15380179]
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</div>
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[[Category: Medicago sativa]]
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<div class="pdbe-citations 1u0w" style="background-color:#fffaf0;"></div>
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[[Category: Naringenin-chalcone synthase]]
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[[Category: Single protein]]
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[[Category: Austin, M.B.]]
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[[Category: Bowman, M.E.]]
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[[Category: Ferrer, J.L.]]
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[[Category: Noel, J.P.]]
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[[Category: Schroder, J.]]
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[[Category: STL]]
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[[Category: aldol switch]]
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[[Category: alpha-beta-alpha-beta-alpha fold]]
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[[Category: catalytic triad]]
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[[Category: chalcone synthase]]
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[[Category: chs]]
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[[Category: condensing enzyme]]
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[[Category: engineered resveratrol synthase]]
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[[Category: pks]]
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[[Category: rs]]
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[[Category: stilbene synthase]]
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[[Category: sts]]
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[[Category: thiolase fold]]
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[[Category: type iii polyketide synthase]]
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''Page seeded by [http://ispc.weizmann.ac.il/oca OCA ] on Wed Nov 21 03:45:34 2007''
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==See Also==
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*[[Chalcone synthase|Chalcone synthase]]
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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]]
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[[Category: Medicago sativa]]
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[[Category: Austin MB]]
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[[Category: Bowman ME]]
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[[Category: Ferrer J-L]]
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[[Category: Noel JP]]
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[[Category: Schroder J]]

Current revision

An Aldol Switch Discovered in Stilbene Synthases Mediates Cyclization Specificity of Type III Polyketide Synthases: 18xCHS+resveratrol Structure

PDB ID 1u0w

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