Industrial Biotransformations, Second Edition PDF
Preview Industrial Biotransformations, Second Edition
IndustrialBiotransformations Editedby A.Liese,K.Seelbach,C.Wandrey IndustrialBiotransformations.AndreasLiese,KarstenSeelbach,ChristianWandrey(Eds.) Copyright©2006WILEY-VCHVerlagGmbH&Co.KGaA,Weinheim ISBN:3-527-31001-0 Further Titlesof Interest Aehle,W.(Ed.) Enzymes in Industry ProductionandApplications Second,CompletelyRevisedEdition 2004 ISBN3-527-29592-5 Bommarius,A.S.,Riebel,B.R. Biocatalysis FundamentalsandApplications 2004 ISBN3-527-30344-8 Buchholz,K.,Kasche,V.,Bornscheuer,U.T. Biocatalysts and Enzyme Technology 2005 ISBN3-527-30497-5 Jördening,H.-J.,Winter,J.(Eds.) Environmental Biotechnology 2005 ISBN3-527-30585-8 Brakmann,S.,Schwienhorst,A.(Eds.) Evolutionary Methods in Biotechnology CleverTricksforDirectedEvolution 2004 ISBN3-527-30799-0 Industrial Biotransformations Second, Completely Revised and Extended Edition Edited by Andreas Liese, Karsten Seelbach, Christian Wandrey Editors (cid:1) AllbookspublishedbyWiley-VCHare carefullyproduced.Nevertheless,authors, Prof.Dr.AndreasLiese editors,andpublisherdonotwarrantthe TechnischeUniversitätHamburg-Harburg informationcontainedinthesebooks, InstituteofBiocatalysis includingthisbook,tobefreeoferrors. Denickestr.15 Readersareadvisedtokeepinmindthat 21073Hamburg statements,data,illustrations,procedural Germany detailsorotheritemsmayinadvertently beinaccurate. Dr.KarstenSeelbach LibraryofCongressCardNo.:appliedfor SiegwerkDruckfarbenAG BritishLibraryCataloguing-in-PublicationData Alfred-Keller-Str.55 Acataloguerecordforthisbookisavailable 53721Siegburg fromtheBritishLibrary. Germany Prof.Dr.ChristianWandrey Bibliographicinformationpublishedby DieDeutscheBibliothek ForschungszentrumJülich DieDeutscheBibliothekliststhispublication InstituteofBiotechnology intheDeutscheNationalbibliografie;detailed 52425Jülich Germany bibliographicdataisavailableintheInternetat <http://dnb.ddb.de>. ©2006WILEY-VCHVerlagGmbH&Co.KGaA, FirstEdition2000 Weinheim Second,CompletelyRevisedand Allrightsreserved(includingthoseof ExtendedEdition2006 translationintootherlanguages). Nopartofthisbookmaybereproduced inanyform–nortransmittedortranslated intomachinelanguagewithoutwritten permissionfromthepublishers.Registered names,trademarks,etc.usedinthisbook, evenwhennotspecificallymarkedassuch, arenottobeconsideredunprotectedbylaw. PrintedintheFederalRepublicofGermany. Printedonacid-freepaper. Typesetting Kühn&Weyh,SatzundMedien, Freiburg Printing BetzDruckGmbH,Darmstadt Bookbinding Litges&DopfBuchbindereiGmbH, Heppenheim ISBN-13: 978-3-527-31001-2 ISBN-10: 3-527-31001-0 V Contents Prefacetothefirstedition IX Prefacetothesecondedition XI ListofContributors XII 1 HistoryofIndustrialBiotransformations–DreamsandRealities 1 DurdaVasic-Racki 1.1 Fromthe“FlowerofVinegar”toRecombinantE.Coli–TheHistoryof MicrobialBiotransformations 1 1.2 FromGastricJuicetoSweetzymeT–TheHistoryofEnzymatic Biotransformations 11 1.3 FromWineBottletoaState-of-the-ArtFacility–TheHistoryof BiochemicalEngineering 23 1.4 AdvantagesofBiotransformationsOverClassicalChemistry-Enzymes areproteins,thingsofbeautyandajoyforever 29 2 TheEnzymeClassification 37 ChristophHohandMurilloVillelaFilho 2.1 EnzymeNomenclature 37 2.2 EnzymeClasses 39 2.2.1 EC1Oxidoreductases 40 2.2.2 EC2Transferases 46 2.2.3 EC3Hydrolases 49 2.2.4 EC4Lyases 54 2.2.5 EC5Isomerases 56 2.2.6 EC6Ligases 59 IndustrialBiotransformations.AndreasLiese,KarstenSeelbach,ChristianWandrey(Eds.) Copyright©2006WILEY-VCHVerlagGmbH&Co.KGaA,Weinheim ISBN:3-527-31001-0 VI Contents 3 RetrosyntheticBiocatalysis 63 JunhuaTao,AlanPettman,andAndreasLiese 3.1 Alkanes 63 3.2 Alkenes 64 3.3 Amines 64 3.4 Alcohols 65 3.5 Aldehydes 67 3.6 Ketones 68 3.7 Epoxides 68 3.8 Diols 69 3.9 CarboxylicAcids 70 3.10 Esters 72 3.11 Amides 72 3.12 Imines 73 3.13 AminoAcids 74 3.14 HydroxyAcids 77 3.15 a-HydroxyKetones 79 3.16 b-HydroxyAldehydes,KetonesorCarboxylicAcids 80 3.17 Cyanohydrins,HemithioacetalsandHemiaminals 81 3.18 SulfoxidesandSulfones 82 3.19 Halides 82 3.20 Aromatics(RingFunctionalization) 83 3.21 CyclicCompounds 84 3.22 Carbohydrates 84 3.23 Peroxides 85 3.24 Isomers 85 3.25 ExamplesofRetrosyntheticBiotransformations 86 3.25.1 Example1 86 3.25.2 Example2 87 4 OptimizationofIndustrialEnzymesbyMolecularEngineering 93 ThorstenEggert 4.1 Introduction 93 4.2 LearningfromNature 95 4.3 EnzymeProductionUsingBacterialExpressionHosts 95 4.4 ImprovementstoEnzymesbyMolecularEngineeringTechniques 98 4.4.1 RationalEnzymeDesign 98 4.4.2 DirectedEvolution 100 4.4.3 RandomMutagenesisMethods 102 4.5 IdentificationofImprovedEnzymeVariants 105 4.6 ConclusionsandFutureProspects 108 Contents VII 5 BasicsofBioreactionEngineering 115 NagarajN.Rao,StephanLütz,KarstenSeelbach,andAndreasLiese 5.1 Definitions 116 5.1.1 ProcessDefinitions 116 5.1.2 DefinitionsofUnitOperations 121 5.2 BiocatalystKinetics 124 5.2.1 TypesofBiocatalysts 124 5.2.2 EnzymeStructure 124 5.2.3 Kinetics 125 5.3 BasicReactorTypesandtheirModesofOperation 130 5.3.1 MassandEnergyBalances 133 5.4 BiocatalystRecyclingandRecovery 135 5.4.1 Entrapment 137 5.4.2 Cross-linking 139 5.4.3 CovalentBinding 139 5.4.4 MembraneFiltration 140 5.5 ReactionParameters 140 5.6 Scale-upofBioreactors 141 5.7 RecentDevelopmentsandTrends 141 6 Processes 147 AndreasLiese,KarstenSeelbach,ArneBuchholz,andJürgenHaberland OxireductasesEC1 153 TransferasesEC2 264 HydrolasesEC3 273 LyasesEC4 447 IsomerasesEC5 503 7 QuantitativeAnalysisofIndustrialBiotransformation 515 AdrieJ.J.Straathof Index Indexofenzymename 521 Indexofstrain 526 Indexofcompany 531 Indexofstartingmaterial 536 Indexofproduct 545 IX Preface to the first edition The main incentive in writing this book was to gather information on one-step biotransformations that are of industrial importance. With this collection, we wanttoillustratethatmoreenzyme-catalyzedprocesseshavegainedpracticalsig- nificancethantheirpotentialusersareconsciousof.Thereisstillaprejudicethat biotransformations are only needed in cases where classical chemical synthesis fails. Even the conviction that the respectivebiocatalysts are not available and, if so, then too expensive, unstable and only functional in water, still seems to be widespread. We hope that this collection of industrial biotransformationswill in future influence decision-makingof synthesisdevelopment in such a way that it might lead to consideringthe possibleincorporationof a biotransformationstep inaschemeofsynthesis. We therefore took great pains in explicitly describing the substrates, the cata- lyst, the product and as much of the reaction conditions as possible of the pro- cessesmentioned.Whereverflowschemeswereavailableforpublicationorcould begeneratedfromthereactiondetails,thiswasdone.Detailsofsomeprocesspa- rameters are still incomplete, since such information is only sparingly available. Weareneverthelessconvincedthatthedetailsaresufficienttoconveyafeelingfor theprocessparameters.Finally,theuseoftheproductsisdescribedandafewpro- cess-relevantreferencesaremade. Wewouldgobeyondthescopeofthisforeword,shouldweattempttothankall thosewhowerekindenoughtosupplyuswithexamples.Ofcourse,weonlypub- lishedopenlyavailableresults(includingthepatentliterature)orusedpersonally conveyedresults with the consentof the respectiveauthors. We are aware of the fact that far more processes exist and that by the time the book is published, many processdetailswillbeoutdated.Nonetheless,webelievethat thiscompila- tion with its overview character will serve the above-mentioned purpose. This awareness could be augmented if the reader, using his or her experience, would take the trouble of filling out the printed worksheet at the end of this bookwith suggestions that could lead to an improvement of a given process or the incor- porationofafurtherindustrialprocessintothecollection. Requesting our industrial partners to make process schemes and parameters moreaccessibledidnotpleasethemverymuch.Evenso,weareaskingourpart- nersonceagaintodisclosemoreinformationthantheyhavedoneinthepast.In IndustrialBiotransformations.AndreasLiese,KarstenSeelbach,ChristianWandrey(Eds.) Copyright©2006WILEY-VCHVerlagGmbH&Co.KGaA,Weinheim ISBN:3-527-31001-0 X Prefacetothefirstedition manyinstances,farmoreknowledgeofindustrialprocesseshasbeengainedthan ispubliclyavailable.Ourobjectiveistobeabletomakeuseofthese“wellknown secrets”aswell.Wewouldliketoexpressourgratitudetoallthosewhosupplied us with information in a progress-conducive manner. Thanks also go to those whodidnotrejectourrequestscompletelyandatleastsupplieduswithaphoto- graphincompensationfortheactuallyrequestedinformation. The book begins with a short historical overview of industrial biotransforma- tions.Sincetheprocessorderofthecompilationisinaccordancewiththeenzyme nomenclature system, the latter is described in more detail. We also include a chapter on reaction engineering to enable an easier evaluation of the processes. The mainpart ofthe book,asyou wouldexpect,isthe compilationofthe indus- trial biotransformations. The comprehensive index will allow a facile search for substrates,enzymesandproducts. Wesincerelyhopethatthisbookwillbeofassistanceintheacademicaswellas the industrial field, when onewants to get an insight into industrial biotransfor- mations. We would be very thankful to receive any correction suggestions or further comments and contributions. At least we hope to experience a trigger effectthatwouldmakeitworthwhileforthereadership,theauthorsandtheedi- torstohaveasecondeditionsucceedingthefirst. We are indebted to several coworkers for screening literature and compiling data,especiallytoJürgenHaberland,DorisHahn,MarianneHess,WolfgangLan- ters,MonikaLauer,ChristianLitterscheid,NagarajRao,DurdaVasic-Racki,Mur- illoVillelaFilho,PhilomenaVolkmannandAndreaWeckbecker. Wethank especiallyUtaSeelbachfordrawingmostofthefiguresduringlong nights, as well as Nagaraj Rao and the “enzyme group” (Nils Brinkmann, Lasse Greiner,JürgenHaberland,ChristophHoh,DavidKihumbu,StephanLaue,Tho- masStillgerandMurilloVillelaFilho). Andlastbutnotleastwethankourfamiliesfortheirsupportandtolerancedur- ingthetimethatweinvestedinoursocalled‘bookproject’. XI Preface to the second edition After more than five years since the first edition of “Industrial Biotransforma- tions” many new examples have become industrially relevant, others have lost importance.Thereforewehadtoenlargethechapter“Processes”by20%.Ifnew informationabouttheprocessesofthefirsteditionwasavailable,thisinformation was incorporated. All processes were checked with respect to the literature (includingpatentliterature).Wehaveincludedallthevaluablecorrectionssugges- tions or further comments and contributions of many readers. This might per- hapsbeofgreatimportanceforthereaderofthesecondedition.Expectingthata firsteditioncouldnotbeperfect,westatedintheprefacetothefirstedition:“We wouldbeverythankfultoreceiveanycorrectionsuggestionsorfurthercomments andcontributions.Atleastwehopetoexperienceatriggereffectthatwouldmake itworthwhileforthereadership,theauthorsandtheeditorstohaveasecondedi- tion succeeding the first.” We were astonished how carefully many readers checked the information given. So the readerof the secondedition will not only have an enlarged chapter “Processes”, but also an updated version with – me must admit – many useful corrections. The best criticism will be given by an experiencedreader.Wehopeverymuchthatthe“old”andthe“new”readerswill realizethatthesecondeditionismorethanaremakeofthefirstedition. Sincethefirsteditionwassoldoutearlierthanwehadexpected,thepublisher founditscientifically–andeconomically–morereasonabletohaveasecondedi- tionthantohaveareprintofthefirstedition.Finallyafteralltheadditionalwork wasdoneweagreedwiththepublisher.Perhapsitisworthtobementionedthat inthemeantimealsothefirstChineseeditionappeared. Thefocusofthebookisstillthechapter“Processes”.Neverthelessalltheother chapterswerecarefullyreevaluated.Inthechapter“HistoryofIndustrialBiotrans- formations”weincludedanewpart“HistoryofBiochemicalEngineering”. Entirelynewisthechapter“RetrosyntheticBiocatalysis”.Thebasicideacomes fromclassicalorganicchemistry, where a complexchemical structureisreduced to building blocks, which might even be commercially available. Similarly, one canfindoutwhicheasilyavailablebuildingblockscanbeusedforindustrialbio- transformations.Wehopethatthereaderwillfindthisconceptuseful.Especially wehopethattheclassicalorganicchemistrybecomesmorepartofbiotechnology thisway. IndustrialBiotransformations.AndreasLiese,KarstenSeelbach,ChristianWandrey(Eds.) Copyright©2006WILEY-VCHVerlagGmbH&Co.KGaA,Weinheim ISBN:3-527-31001-0
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