Natural Products via Enzymatic Reactions PDF
Preview Natural Products via Enzymatic Reactions
297 Topics in Current Chemistry Editorial Board: A. de Meijere K.N. Houk C.A. Hunter H. Kessler l l l J.-M. Lehn S.V. Ley M. Olivucci J. Thiem B.M. Trost l l l l M. Venturi P. Vogel H. Wong H. Yamamoto l l l Topics in Current Chemistry Recently Published and Forthcoming Volumes NaturalProductsviaEnzymaticReactions TemplatesinChemistryIII VolumeEditor:Jo¨rnPiel VolumeEditors:Broekmann,P.,Do¨tz,K.-H., Vol.297,2010 Schalley,C.A. Vol.287,2009 NucleicAcidTransfection VolumeEditors:WolfgangBielke, Tubulin-BindingAgents: ChristophErbacher Synthetic,StructuralandMechanisticInsights Vol.296,2010 VolumeEditor:Carlomagno,T. CarbohydratesinSustainableDevelopmentII Vol.286,2009 VolumeEditors:Ame´liaP.Rauter, PierreVogel,YvesQueneau STMandAFMStudieson(Bio)molecular Vol.295,2010 Systems:UnravellingtheNanoworld VolumeEditor:Samor`ı,P. CarbohydratesinSustainableDevelopmentI Vol.285,2008 VolumeEditors:Ame´liaP.Rauter, PierreVogel,YvesQueneau Vol.294,2010 AmplificationofChirality VolumeEditor:Soai,K. FunctionalMetal-OrganicFrameworks:Gas Vol.284,2008 Storage,SeparationandCatalysis VolumeEditor:MartinSchro¨der AnthracyclineChemistryandBiologyII Vol.293,2010 ModeofAction,ClinicalAspectsandNewDrugs C-HActivation VolumeEditor:Krohn,K. VolumeEditors:Jin-QuanYu,ZhangjieShi Vol.283,2008 Vol.292,2010 AnthracyclineChemistryandBiologyI AsymmetricOrganocatalysis BiologicalOccurenceandBiosynthesis, VolumeEditor:BenjaminList SynthesisandChemistry Vol.291,2010 VolumeEditor:Krohn,K. IonicLiquids Vol.282,2008 VolumeEditor:BarbaraKirchner Vol.290,2010 PhotochemistryandPhotophysicsof CoordinationCompoundsII OrbitalsinChemistry VolumeEditors:Balzani,V.,Campagna,S. VolumeEditor:SatoshiInagaki Vol.281,2007 Vol.289,2009 GlycoscienceandMicrobialAdhesion PhotochemistryandPhotophysicsof VolumeEditors:ThisbeK.Lindhorst, CoordinationCompoundsI StefanOscarson VolumeEditors:Balzani,V.,Campagna,S. Vol.288,2009 Vol.280,2007 Natural Products via Enzymatic Reactions Volume Editor: Jo¨rn Piel With Contributions by I. Abe (cid:1) A. Bechthold (cid:1) Z. Chen (cid:1) V. Fedorenko (cid:1) T. Fischer (cid:1) T.A.M. Gulder (cid:1) B.S. Moore (cid:1) B. Ostash (cid:1) J. Pietruszka (cid:1) A.A. Roberts (cid:1) M. Ruppert (cid:1) K.S. Ryan (cid:1) J. Sto¨ckigt (cid:1) X. Yan Editor Prof.Dr.Jo¨rnPiel Universita¨tBonn Kekule´-Institutfu¨rOrganische ChemieundBiochemie Gerhard-Domagk-Str.1 53121Bonn Germany [email protected] ISSN0340-1022 e-ISSN1436-5049 ISBN978-3-642-16426-2 e-ISBN978-3-642-16427-9 DOI10.1007/978-3-642-16427-9 SpringerHeidelbergDordrechtLondonNewYork LibraryofCongressControlNumber:2010938783 #Springer-VerlagBerlinHeidelberg2010 Thisworkissubjecttocopyright.Allrightsarereserved,whetherthewholeorpartofthematerialis concerned,specificallytherightsoftranslation,reprinting,reuseofillustrations,recitation,broadcasting, reproductiononmicrofilmorinanyotherway,andstorageindatabanks.Duplicationofthispublication orpartsthereofispermittedonlyundertheprovisionsoftheGermanCopyrightLawofSeptember9, 1965,initscurrentversion,andpermissionforusemustalwaysbeobtainedfromSpringer.Violations areliabletoprosecutionundertheGermanCopyrightLaw. 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Coverdesign:WMXDesignGmbH,Heidelberg,Germany Printedonacid-freepaper SpringerispartofSpringerScience+BusinessMedia(www.springer.com) Volume Editor Prof.Dr.Jo¨rnPiel Universita¨tBonn Kekule´-Institutfu¨rOrganische ChemieundBiochemie Gerhard-Domagk-Str.1 53121Bonn Germany [email protected] Editorial Board Prof.Dr.ArmindeMeijere Prof.Dr.Jean-MarieLehn Institutfu¨rOrganischeChemie ISIS derGeorg-August-Universita¨t 8,alle´eGaspardMonge Tammanstr.2 BP70028 37077Go¨ttingen,Germany 67083StrasbourgCedex,France [email protected] [email protected] Prof.Dr.KendallN.Houk Prof.Dr.StevenV.Ley UniversityofCalifornia UniversityChemicalLaboratory DepartmentofChemistryandBiochemistry LensfieldRoad 405HilgardAvenue CambridgeCB21EW LosAngeles,CA90024-1589,USA GreatBritain [email protected] [email protected] Prof.Dr.ChristopherA.Hunter Prof.Dr.MassimoOlivucci DepartmentofChemistry Universita`diSiena UniversityofSheffield DipartimentodiChimica SheffieldS37HF,UnitedKingdom ViaADeGasperi2 c.hunter@sheffield.ac.uk 53100Siena,Italy [email protected] Prof.Dr.HorstKessler Prof.Dr.JoachimThiem Institutfu¨rOrganischeChemie TUMu¨nchen Institutfu¨rOrganischeChemie Lichtenbergstraße4 Universita¨tHamburg 86747Garching,Germany Martin-Luther-King-Platz6 [email protected] 20146Hamburg,Germany [email protected] vi EditorialBoard Prof.Dr.BarryM.Trost Prof.Dr.HenryWong DepartmentofChemistry TheChineseUniversityofHongKong StanfordUniversity UniversityScienceCentre Stanford,CA94305-5080,USA DepartmentofChemistry [email protected] Shatin,NewTerritories [email protected] Prof.Dr.MargheritaVenturi Prof.Dr.HisashiYamamoto DipartimentodiChimica Universita`diBologna ArthurHollyComptonDistinguished viaSelmi2 Professor 40126Bologna,Italy DepartmentofChemistry [email protected] TheUniversityofChicago 5735SouthEllisAvenue Prof.Dr.PierreVogel Chicago,IL60637 773-702-5059 LaboratoryofGlycochemistry USA andAsymmetricSynthesis [email protected] EPFL–Ecolepolytechniquefe´derale deLausanne EPFLSBISICLGSA BCH5307(Bat.BCH) 1015Lausanne,Switzerland pierre.vogel@epfl.ch Topics in Current Chemistry Also Available Electronically Topics in Current Chemistry is included in Springer’s eBook package Chemistry andMaterialsScience.Ifalibrarydoesnotoptforthewholepackagethebookseries may be bought on a subscription basis. 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InreferencesTopicsinCurrentChemistryisabbreviatedTop CurrChemandis citedasajournal. ImpactFactor2009:4.291;Section“Chemistry,Multidisciplinary”:Rank20of138 Preface Natural products are one of the major sources of today’s drugs. In addition, they provide intriguing insights into the taxonomy, evolution, biochemistry and social behavioroforganisms,andtheirremarkablestructuralandbiogeneticdiversityand pharmacologicalpropertiesarearichinspirationforsyntheticchemists.Tradition- ally,naturalproductswerepreparedinthelaboratorybyorganicsyntheticstrategies usingsmallmoleculesasreagents.Thissituationhaschangedtoday,sinceenzymes are incorporated into many synthetic routes at the research and industrial scale. Enzymespossessseveraladvantagesovermostclassicalreagents:theyarenontox- ic, can be used at mild conditions and often exhibit exquisite stereo- and regios- electivity. These properties make them ideally suited to aid the construction of complex molecular scaffolds of natural products and their analogues. To fully exploittheirpotential,researchattheinterfaceofbiochemistry,moleculargenetics and organic synthesis is necessary. Biosynthetic studies uncover enzymatic cata- lysts with remarkable properties, such as fluorination “reagents”, Diels-Alderases andmultimodularenzymes,whereasingleproteincancatalyzedozensofindivid- ualreactions.Molecularbiologistsdevelopnovelmethods bywhichenzymescan be improved in terms of substrate range, stability and turnover. In the field of synthesis, the concept of “total biosynthesis” has emerged, in which natural pro- ductsaregeneratedinvitrousingexclusivelyenzymes.Insightsgainedintoenzy- maticstructureandmechanismalsoheavilyinspirescientistsinorganiccatalysisand supramolecularchemistrytodevelopincreasinglycomplexandefficientenzyme-like synthetictools. This volume entitled “Natural Products via Enzymatic Reactions” presents the current status of selected areas of this broad discipline. Contributors who are leadersintheirfieldsreviewenzymaticmethodologyandtherangeofapplications fornaturalproductsynthesis.Individualnaturalproductclasses,suchasalkaloids, polyketides or carbohydrates, will be individually discussed to provide deeper insights into biosynthetic pathways and their potential to generate known and novel compounds. Finally, synthetic strategies of chemists and nature are com- pared, and recent breakthroughs in total biosynthesis will be highlighted. The chaptersreflectthattheseareexcitingtimesforchemistry,whenresearchersfrom ix x Preface diverse methodological backgrounds merge their expertise to create new ways of effectiveandsustainablesynthesis. Bonn,September2010 Jo¨rnPiel UniversityofBonn
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