Structure-function relationships of wheat flavone O-methyltransferase Homology modeling and site-directed mutagenesis 英文参考文献.docVIP

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Structure-function relationships of wheat flavone O-methyltransferase Homology modeling and site-directed mutagenesis 英文参考文献.doc

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Structure-function relationships of wheat flavone O-methyltransferase Homology modeling and site-directed mutagenesis 英文参考文献

Zhouetal.BMCPlantBiology2010,10:156 /1471-2229/10/156 RESEARCH ARTICLE OpenAccess Structure-functionrelationshipsofwheatflavone O-methyltransferase:Homologymodelingand site-directedmutagenesis Jian-MinZhou1?,EunjungLee2?,FrancescaKanapathy-Sinnaiaha1,YoungheePark2,JackAKornblatt3, YoonghoLim2,RagaiKIbrahim1* Abstract Background:Wheat(TriticumaestivumL.)O-methyltransferase(TaOMT2)catalyzesthesequentialmethylationof theflavone,tricetin,toits3′-methyl-(selgin),3′,5′-dimethyl-(tricin)and3′,4′,5′-trimethyletherderivatives.Tricin,a potentialmultifunctionalnutraceutical,isthemajorenzymereactionproduct.Thesesuccessivemethylationsraised thequestionastowhethertheytakeplaceinone,ordifferentactivesites.Weconstructeda3-Dmodelofthis proteinusingthecrystalstructureofthehighlyhomologousMedicagosativacaffeicacid/5-hydroxyferulicacidO- methyltransferase(MsCOMT)asatemplatewiththeaimofproposingamechanismformultiplemethyltransfer reactionsinwheat. Results:ThismodelrevealeduniquestructuralfeaturesofTaOMT2whichpermitthestepwisemethylationof tricetin.SubstratebindingismediatedbyanextensivenetworkofH-bondsandvanderWaalsinteractions. Mutationalanalysisofstructurallyguidedactivesiteresiduesidentifiedthoseinvolvedinbindingandcatalysis.The partlyburiedtricetinactivesite,aswellasproximityandorientationeffectsensuredsequentialmethylationofthe substratewithinthesamepocket.Stepwisemethylationoftricetininvolvesdeprotonationofitshydroxylgroupsby aHis262-Asp263pairfollowedbynucleophilicattackofSAM-methylgroups.WealsodemonstratethatVal309, whichisconservedinanumberofgraminaceousflavoneOMTs,definesthepreferenceofTaOMT2fortricetinas thesubstrate. Conclusions:Weproposeamechanismforthesequentialmethylationoftricetin,anddiscussthepotential applicationofTaOMT2toincreasetheproductionoftricinasanutraceutical.Thesingleaminoacidresiduein TaOMT2,Val309,determinesitspreferencefortricetinasthesubstrate,andmaydefinetheevolutionarydifferences betweenthetwocloselyrelatedproteins,COMTandflavoneOMT. Background with c