天然药物化学第二讲PPT推荐.ppt
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天然药物化学第二讲PPT推荐.ppt
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IntroductiontotheStudiesofBiosynthesisofNaturalProductsYuemaoSCollegeofPharmaceuticalSciences,ShandongUniversitySeptember13,20103.ThreeexamplesTheBiosynthesisofTaxolTechniquesweapplied:
@#@A.Stableisotopelabeling,feedingB.RadioactiveisotopetracinginEnzymaticacetylationConclusion:
@#@10-deacetylbaccatin-IIIisaprecursoroftaxolHypotheticmultiplepathwaystowardstaxolThebiosynthesisofrifamycinBTwopossiblepathways,AandB,towardsrifamycinB.AdemandedthatprotorifamycinIisthekeyintermediateandtheoxygenattheC-8positionisintroducedlater.BrequiredthattheoxygenatC-8isofthesameoriginasthecarbonofC-8,i.e.,fromthecarboxylgroupofAHBA.MethodsandTechiques:
@#@DNAmutagensis;@#@stableisotopelabeling,feeding;@#@13CNMRassay;@#@LC-ESI-MSConclusions:
@#@A.TheC-8oxygenisthesameoriginastheC-8carbonB.TheformationofnaphthoquinoneprecedesthelactamizationC.ThebiosynthesisoftypeIpolyketidesoccursprogressivelyThesequenceoftheformationofthenaphthoquinoneandlactamThebiosynthesisofStreptomycessporepigmentOriginsofBuildingBlocksCommonBuildingBlocksC1C2C5CommonBuildingBlocksC6C3C6C2C6C1C6C2NCommonBuildingBlocksC4NC5NIndole-C2NCommonFAsAcylThioesterGeneralChemistryAldolandClaisenCondensationAldolandClaisenCondensationAldolandClaisenCondensationMalonylCoA:
@#@activatedacetylCoAMalonylCoA:
@#@activatedacetylCoAOverallBiosyntheticSchemeBacterialAromaticPolyketidesBacterialAromaticPolyketidesBacterialAromaticPolyketidesBacterialReducedPolyketidesA,Acetate;@#@P,Propionate;@#@B,Butyrate;@#@G,Glycerol;@#@S,StarterfrombranchedchainorcyclicunitsBacterialReducedPolyketidesBacterialReducedPolyketidesFungalAromaticPolyketides(Non-reduced/PartiallyReducedPolyketides)OrsellinicacidTetrahydroxynaphthalene(THN)6-Methylsalicylicacid(MSA)NorsolorinicacidFungalAromaticPolyketideswithunusualfeatures-mixedreduced/non-reducedUnusualacetatelabelUnusualstarterUnusualmixFungalHighlyReducedPolyketidesT-toxinMevacorStatinshydroxy-methylglutaryl-CoA(HMG-CoA).FungalAromaticPolyketides(Non-reduced/PartiallyReducedPolyketides)OrsellinicacidTetrahydroxynaphthalene(THN)6-Methylsalicylicacid(MSA)NorsolorinicacidPlantPolyketides(BacterialpolyketidesmadebythesametypeofPKS)chalconeinhigherplants1,3,6,8-tetrahydroxynaphthalene(THN)inStreptomycesgriseusandS.coelicolor3,5-dihydroxyphenylaceticacid(DHPA)inAmycolatopsismediterraneiandA.orientalisPlantPolyketides(Starter:
@#@PhenylpropanhoidPathway)chalconePlantPolyketides(BacterialpolyketidesmadebythesametypeofPKS)chalconeinhigherplants1,3,6,8-tetrahydroxynaphthalene(THN)inStreptomycesgriseusandS.coelicolor3,5-dihydroxyphenylaceticacid(DHPA)inAmycolatopsismediterraneiandA.orientalisNonribosomalPeptidesAntibioticsNonribosomalPeptidesAntibioticsNonribosomalPeptidesImmunosuppresantsNonribosomalPeptidesToxinsNonribosomalPeptidesNonribosomalPeptidesNonribosomalPeptidesNonribosomalPeptidesNonribosomalPeptidesNonribosomalPeptidesAntibioticsNonribosomalPeptidesAntibioticsNonribosomalPeptidesLastresortforagainstdrug-resistantpathogensNonribosomalPeptidesHybridNRP-PKNonribosomalPeptidesHybridNRP-PK-C-aminatedNonribosomalPeptidesHybridNRP-PK-N-acylatedNonribosomalPeptides
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