Comprehensive Natural Products II: Chemistry and Biology: Carbohydrates, Nucleosides & Nucleic Acids PDF
Preview Comprehensive Natural Products II: Chemistry and Biology: Carbohydrates, Nucleosides & Nucleic Acids
Contents of all Volumes ContributorstoallVolumes xvii Preface xxxvii Introduction xxxix Editors-in-Chief xliii VolumeEditors xlv Volume1 NaturalProductsStructuralDiversity-ISecondaryMetabolites: OrganizationandBiosynthesis 01 OverviewandIntroduction 1 CraigA.Townsend,JohnsHopkinsUniversity,Baltimore,MD,USA 02 UnsaturatedFattyAcids 5 PeterH.Buist,CarletonUniversity,ON,Canada 03 ProstaglandinEndoperoxideSynthases:Structure,Function,andSynthesisofNovelLipid SignalingMolecules 35 MelissaV.TurmanandLawrenceJ.Marnett,VanderbiltUniversitySchoolofMedicine, Nashville,TN,USA 04 MycolicAcid/CyclopropaneFattyAcid/FattyAcidBiosynthesisandHealthRelations 65 DavidB. Kastrinsky,NicholasS.McBride,KeriannM.Backus,JasonJ.LeBlanc,and CliftonE.Barry,III,NationalInstitutesofHealth,Bethesda,MD,USA 05 MicrobialTypeIIIPolyketideSynthases 147 YoheiKatsuyamaandSueharuHorinouchi,TheUniversityofTokyo,Bunkyo-ku,Tokyo,Japan 06 PlantTypeIIIPKS 171 HiroyukiMoritaandIkuroAbe,TheUniversityofTokyo,Hongo,Tokyo,Japan HiroshiNoguchi,UniversityofShizuoka,Yada,Shizuoka,Japan 07 TypeIIPKS 227 Ju¨rgenRohr,UniversityofKentucky,Lexington,KY,USA ChristianHertweck,LeibnizInstituteforNaturalProductResearchandInfectionBiology, HKI,Jena,Germany 08 StructuralEnzymologyofPolyketideSynthase:TheStructure–Sequence–FunctionCorrelation 305 TylerPazKorman,BrianAmes,andShiou-Chuan(Sheryl)Tsai,UniversityofCalifornia, Irvine,CA,USA 09 FungalTypeIPolyketides 347 RussellJ.CoxandThomasJ.Simpson,UniversityofBristol,Bristol,UK 10 TypeIModularPKS 385 AlisonM.Hill,UniversityofExeter,Exeter,UK JamesStaunton,UniversityofCambridge,Cambridge,UK v vi ContentsofallVolumes 11 NRPS/PKSHybridEnzymesandTheirNaturalProducts 453 ChristopherM.Rath,JamieB.Scaglione,JeffreyD.Kittendorf,andDavidH.Sherman, LifeSciencesInstituteUniversityofMichigan,AnnArbor,MI,USA 12 MevalonatePathwayinBacteriaandArchaea 493 TomohisaKuzuyama,TheUniversityofTokyo,Tokyo,Japan HisashiHemmi,NagoyaUniversity,Nagoya,Japan ShunjiTakahashi,RIKEN,AdvancedScienceInstitute,Saitama,Japan 13 MethylerythritolPhosphatePathway 517 MichelRohmer,Universite´deStrasbourg/CNRS,Strasbourg,France 14 Prenyltransferase 557 HirofumiKurokawaandTanetoshiKoyama,TohokuUniversity,Sendai,Japan 15 AdvancesintheEnzymologyofMonoterpeneCyclizationReactions 585 EdwardM.Davis,WashingtonStateUniversity,Pullman,WA,USA 16 Sesquiterpenes 609 JoeChappell,UniversityofKentucky,Lexington,KY,USA RobertM.Coates,UniversityofIllinois,Urbana,IL,USA 17 Diterpenes 643 TomonobuToyomasuandTakeshiSassa,YamagataUniversity,Tsuruoka,Japan 18 Triterpenes 673 TetsuoKushiroandYutakaEbizuka,TheUniversityofTokyo,Tokyo,Japan 19 BacterialSqualeneCyclase 709 IkuroAbe,TheUniversityofTokyo,Hongo,Tokyo,Japan 20 Carotenoids 733 NorihikoMisawa,KirinHoldingsCo.Ltd.,Nonoichi-machi,Ishikawa,Japan 21 SterolandSteroidBiosynthesisandMetabolisminPlantsandMicroorganisms 755 HubertSchaller,Universite´deStrasbourgandCNRS,Strasbourg,France 22 IsoprenoidinActinomycetes 789 TohruDairi,ToyamaPrefecturalUniversity,Toyama,Japan 23 Lignans(Neolignans)andAllyl/PropenylPhenols:Biogenesis,StructuralBiology,and Biological/HumanHealthConsiderations 815 DanielG.Vassa˜o,Kye-WonKim,LaurenceB.Davin,andNormanG.Lewis, WashingtonStateUniversity,Pullman,WA,USA 24 PlantPhenolics:Phenylpropanoids 929 Shin-ichiAyabe,HiroshiUchiyama,ToshioAoki,andTomoyoshiAkashi,NihonUniversity, Fujisawa,Japan 25 Alkaloids 977 SarahE.O’Connor,MassachusettsInstituteofTechnology,Cambridge,MA,USA Volume2 NaturalProductsStructuralDiversity-IISecondaryMetabolites: Sources,StructuresandChemicalBiology 01 OverviewandIntroduction 1 BradleyS.Moore,UniversityofCaliforniaatSanDiego,LaJolla,CA,USA PhillipCrews,UniversityofCaliforniaatSantaCruz,SantaCruz,CA,USA 02 TerrestrialPlantsasaSourceofNovelPharmaceuticalAgents 5 GordonM.CraggandDavidJ.Newman,NCI-Frederick,Frederick,MD,USA DavidG.I.Kingston,VirginiaPolytechnicInstitute&StateUniversity,Blacksburg,VA,USA ContentsofallVolumes vii 03 MarineMacroalgalNaturalProducts 41 E.PaigeStoutandJuliaKubanek,GeorgiaInstituteofTechnology,Atlanta,GA,USA 04 InsectNaturalProducts 67 MatthewGronquist,SUNYCollegeatFredonia,Fredonia,NY,USA FrankC.Schroeder,CornellUniversity,Ithaca,NY,USA 05 TerrestrialMicroorganisms–FilamentousBacteria 109 SheoB.Singh,MerckResearchLaboratories,Rahway,NJ,USA OlgaGenilloudandFernandoPela´ez,CIBE,MerckSharp&DohmedeEspan˜a,Madrid,Spain 06 TheNaturalProductsChemistryofCyanobacteria 141 KevinTidgewell,BenjaminR.Clark,andWilliamH.Gerwick,UniversityofCalifornia SanDiego,LaJolla,CA,USA 07 Myxobacteria–UniqueMicrobialSecondaryMetaboliteFactories 189 SilkeC.WenzelandRolfMu¨ller,SaarlandUniversity,Saarbru¨cken,Germany 08 NaturalProductDiversityfromMarineFungi 223 RainerEbel,UniversityofAberdeen,Aberdeen,UK 09 BioactiveMetabolitesfromMarineDinoflagellates 263 Jun’ichiKobayashiandTakaakiKubota,HokkaidoUniversity,Sapporo,Japan 10 MarineInvertebrates:Sponges 327 YoichiNakao,WasedaUniversity,Tokyo,Japan NobuhiroFusetani,HokkaidoUniversity,Hakodate,Japan 11 TheNaturalProductsChemistryoftheGorgonianGenusPseudopterogorgia(Octocorallia: Gorgoniidae) 363 JeffreyMarrero,IleanaI.Rodr´ıguez,andAbimaelD.Rodr´ıguez,UniversityofPuertoRico, SanJuan,PR,USA 12 ExploitingGenomicsforNewNaturalProductDiscoveryinProkaryotes 429 ChristopheCorreandGregoryL.Challis,UniversityofWarwick,Coventry,UK 13 UnlockingEnvironmentalDNADerivedGeneClustersUsingaMetagenomicsApproach 455 JeffreyH.Kim,T.LukeSimmons,andSeanF.Brady,TheRockefellerUniversity, NewYork,NY,USA 14 TheChemistryofSymbioticInteractions 475 Jo¨rnPiel,UniversityofBonn,Bonn,Germany 15 NaturalPeptideToxins 511 FrankMar´ı,FloridaAtlanticUniversity,BocaRaton,FL,USA JanTytgat,UniversityofLeuven,Leuven,Belgium 16 Cyanobactins–UbiquitousCyanobacterialRibosomalPeptideMetabolites 539 MohamedS.DoniaandEricW.Schmidt,UniversityofUtah,SaltLakeCity,UT,USA 17 TheRoleofSynthesisandBiosyntheticLogic 559 YousongDingandDavidH.Sherman,TheUniversityofMichigan,AnnArbor,MI,USA 18 MissasignedStructures:CaseExamplesfromthePastDecade 581 TaroAmagata,SanFranciscoStateUniversity,SanFrancisco,CA,USA 19 NaturalProductsofTherapeuticImportance 623 DavidJ.NewmanandGordonM.Cragg,NCI-Frederick,Frederick,MD,USA 20 NaturalProductsasProbesofSelectedTargetsinTumorCellBiologyandHypoxicSignaling 651 DaleG.NagleandYu-DongZhou,UniversityofMississippi,University,MS,USA viii ContentsofallVolumes Volume3 Development&ModificationofBioactivity 01 OverviewandIntroduction 1 RobVerpoorte,LeidenUniversity,Leiden,TheNetherlands 02 NaturalProductsasLeadSourcesforDrugDevelopment 5 StefanWetzel,HugoLachance,andHerbertWaldmann,MaxPlanckInstituteofMolecularPhysiology, Dortmund,Germany 03 TopicalChemicalSpaceRelationtoBiologicalSpace 47 AndersBacklund,UppsalaUniversity,Uppsala,Sweden 04 TheNAPRALERTDatabaseasanAidforDiscoveryofNovelBioactiveCompounds 81 JamesG.GrahamandNormanR.Farnsworth,UniversityofIllinoisatChicago,Chicago,IL,USA 05 PlantDiversityfromBrazilianCerradoandAtlanticForestasaToolforProspectingPotential TherapeuticDrugs 95 DulceHelenaSiqueiraSilva,IanCastro-Gamboa,andVanderlanDaSilvaBolzani,Sa˜oPauloState University,Araraquara,Sa˜oPaulo,Brazil 06 NatureasSourceofMedicines;NovelDrugsfromNature;ScreeningforAntitumorActivity 135 GordonM.CraggandDavidJ.Newman,NCI-Frederick,Frederick,MD,USA 07 TheIdentificationofBioactiveNaturalProductsbyHighThroughputScreening(HTS) 177 VickyM.Avery,DavidCamp,AnthonyR.Carroll,IanD.Jenkins,andRonaldJ.Quinn, GriffithUniversity,Brisbane,QLD,Australia 08 NaturalProductsDrugDiscovery 205 GiovanniAppendino,Universita`delPiemonteOrientale,Novara,Italy GabrieleFontana,IndenaS.p.A.,Milano,Italy FedericaPollastro,Universita`delPiemonteOrientale,Novara,Italy 09 NaturalProduct-BasedBiopesticidesforInsectControl 237 AzucenaGonzalez-Coloma,InstitutodeCienciasAgrarias-CCMA,Madrid,Spain Mat`ıasReina,CarmenE.Diaz,andBraulioM.Fraga,InstitutodeProductosNaturalesy Agrobiologia,Tenerife,Spain 10 NaturalProductsasSweetenersandSweetnessModifiers 269 A.DouglasKinghorn,Young-WonChin,andLiPan,TheOhioStateUniversity,Columbus,OH,USA ZhonghuaJia,GivaudanFlavorsCorporation,Cincinnati,OH,USA 11 ChemistryofCosmetics 317 MasahiroOtaandMineyukiYokoyama,ShiseidoCo.,Ltd.,Yokohama,Japan 12 EthnopharmacologyandDrugDiscovery 351 MichaelHeinrich,UniversityofLondon,London,UK 13 ChineseTraditionalMedicine 383 MinYang,SijiaTao,ShuhongGuan,XiaohuiWu,PingpingXu,andDe-anGuo, ShanghaiInstituteofMateriaMedica,Shanghai,China 14 AyurvedainModernMedicine:DevelopmentandModificationofBioactivity 479 PulokK.Mukherjee,M.Venkatesh,andArunavaGantait,JadavpurUniversity,Kolkata,India 15 BiologicallyActiveCompoundsinFoodProductsandTheirEffectsonObesityandDiabetes 509 RengerF.Witkamp,WageningenUniversityandTNOQualityofLife,Wageningen,TheNetherlands 16 ChemistryofFlavonoid-BasedColorsinPlants 547 ØyvindM.AndersenandMonicaJordheim,UniversityofBergen,Bergen,Norway 17 ProductionofPharmaceuticalsbyPlantTissueCultures 615 ToshiyaMuranaka,YokohamaCityUniversity,Yokohama,Japan,RIKENPlantScienceCenter, Yokohama,Japan KazukiSaito,ChibaUniversity,Chiba,Japan,RIKENPlantScienceCenter,Yokohama,Japan ContentsofallVolumes ix 18 PlantSecondaryMetabolismEngineering:Methods,Strategies,Advances,andOmics 629 RafaelZa´rate,TheUniversityofLaLaguna,Tenerife,Spain 19 BiotransformationofMonoterpenoids 669 YoshiakiNomaandYoshinoriAsakawa,TokushimaBunriUniversity,Yamashiro-cho, Tokushima,Japan 20 BiotransformationofSesquiterpenoids 803 YoshinoriAsakawaandYoshiakiNoma,TokushimaBunriUniversity,Yamashiro-cho, Tokushima,Japan 21 BiotransformationofDi-andTriterpenoids,Steroids,andMiscellaneousSyntheticSubstrates 893 YoshinoriAsakawaandYoshiakiNoma,TokushimaBunriUniversity,Yamashiro-cho, Tokushima,Japan 22 BeerFlavor 967 LeenC.Verhagen,UniversityofLeiden,Leiden,TheNetherlands 23 ChemistryofTea 999 UlrichH.Engelhardt,Institutfu¨rLebensmittelchemie,Braunschweig,Germany 24 ChemistryofCannabis 1033 ArnoHazekamp,JustinT.Fischedick,Mo´nicaLlanoD´ıez,AndreaLubbe,and ReneeL.Ruhaak,LeidenUniversity,Leiden,TheNetherlands 25 ChemistryofCoffee 1085 S.Oestreich-Janzen,CAFEAGmbH,Hamburg,Germany 26 ChemistryofWine 1119 Ve´roniqueCheynier,Re´miSchneider,Jean-MichelSalmon,andHe´le`neFulcrand, MontpellierResearchCentre,Montpellier,France 27 Trees:ARemarkableBiochemicalBounty 1173 AnnM.Patten,DanielG.Vassa˜o,MichaelP.Wolcott,LaurenceB.Davin,and NormanG.Lewis,WashingtonStateUniversity,Pullman,WA,USA 28 TheChemistryofArabidopsisthaliana 1297 M.Soledade,C.PedrasandQinganZheng,UniversityofSaskatchewan,Saskatoon,SK,Canada Volume4 ChemicalEcology 01 OverviewandIntroduction 1 KenjiMori,TheUniversityofTokyo,Tokyo,Japan 02 PlantHormones 9 IsomaroYamaguchi,MaebashiInstituteofTechnology,Gunma,Japan JerryD.CohenandAngelaH.Culler,UniversityofMinnesota,Minneapolis,USA MarcelQuint,LeibnizInstituteofPlantBiochemistry,Halle,Germany JanetP.Slovin,UnitedStatesDepartmentofAgriculture,Washington,DC,USA MasatoshiNakajima,TheUniversityofTokyo,Tokyo,Japan ShinjiroYamaguchi,HitoshiSakakibara,andTakeshiKuroha,RIKENPlantScienceCenter, Kanagawa,Japan NobuhiroHirai,KyotoUniversity,Kyoto,Japan TakaoYokota,TeikyoUniversity,Utsunomiya,Japan HiroyukiOhtaandYuichiKobayashi,TokyoInstituteofTechnology,Tokyo,Japan HitoshiMoriandYojiSakagami,NagoyaUniversity,Nagoya,Japan 03 InsectHormones 127 E.DavidMorgan,KeeleUniversity,Staffordshire,UK 04 PheromonesofTerrestrialInvertebrates 153 WittkoFrancke,UniversityofHamburg,Hamburg,Germany StefanSchulz,TechnischeUniversita¨tBraunschweig,Braunschweig,Germany x ContentsofallVolumes 05 PheromonesinVertebrates 225 PeterW.SorensenandThomasR.Hoye,UniversityofMinnesota,Minneapolis,MN,USA 06 PheromonesofMarineInvertebratesandAlgae 263 MasakiKita,UniversityofTsukuba,Tsukuba,Japan MakotoKitamuraandDaisukeUemura,KeioUniversity,Yokohama,Japan 07 Cell-to-CellCommunicationsamongMicroorganisms 283 SueharuHorinouchi,TheUniversityofTokyo,Tokyo,Japan KenjiUeda,NihonUniversity,Kanagawa,Japan JiroNakayama,KyushuUniversity,Fukuoka,Japan TsukasaIkeda,UtsunomiyaUniversity,Tochigi,Japan 08 ChemicalDefenceandToxinsofPlants 339 HisakazuYamane,TheUniversityofTokyo,Tokyo,Japan KotaroKonno,NationalInstituteofAgrobiologicalSciences,Tsukuba,Ibaraki,Japan MauriceSabelis,UniversityofAmsterdam,Amsterdam,TheNetherlands JunjiTakabayashi,KyotoUniversity,Otsu,Shiga,Japan TakeshiSassa,YamagataUniversity,Tsuruoka,Japan HideakiOikawa,HokkaidoUniversity,Sapporo,Japan 09 ChemicalDefenseandToxinsofLowerTerrestrialandFreshwaterAnimals 387 KonradDettner,UniversityofBayreuth,Bayreuth,Germany 10 ToxinsofMicroorganisms 411 ShoheiSakuda,UniversityofTokyo,Tokyo,Japan MakotoKimura,RIKEN,Saitama,Japan 11 TerrestrialNaturalProductsasAntifeedants 457 FalkoP.DrijfhoutandE.DavidMorgan,KeeleUniversity,Staffordshire,UK 12 MarineNaturalProductsasAntifeedants 503 MaryJ.Garson,TheUniversityofQueensland,Brisbane,QLD,Australia 13 AllelochemicalsforPlant–PlantandPlant–MicrobeInteractions 539 KoichiYoneyama,UtsunomiyaUniversity,Utsunomiya,Japan MasahiroNatsume,TokyoUniversityofAgricultureandTechnology,Tokyo,Japan 14 AllelochemicalsinPlant–InsectInteractions 563 KeiichiHondaandHisashiOˆmura,HiroshimaUniversity,Higashihiroshima,Japan MasatoshiHori,TohokuUniversity,Sendai,Japan YooichiKainoh,UniversityofTsukuba,Tsukuba,Japan 15 Human–EnvironmentInteractions(1):FlavorandFragrance 595 MasashiIshikawa,YasuhiroWarita,EisukeTakahisa,andYasutakaOhkubo,T.HasegawaCo., Ltd.,Tokyo,Japan 16 Human–EnvironmentInteractions–Taste 631 KunisukeIzawa,YusukeAmino,MasanoriKohmura,YoichiUeda,andMotonakaKuroda, AjinomotoCo.,Inc.,Kawasaki,Japan Volume5 AminoAcids,PeptidesandProteins 01 OverviewandIntroduction 1 JohnC.Vederas,UniversityofAlberta,Edmonton,AB,Canada 02 NonproteinL-AminoAcids 5 SabesanYoganathanandJohnC.Vederas,UniversityofAlberta,Edmonton,AB,Canada 03 NovelEnzymesforBiotransformationandResolutionofAlpha-AminoAcids 71 PaulC.EngelandFrancescaParadisi,UniversityCollegeDublin,Dublin,Ireland ContentsofallVolumes xi 04 1-Aminocyclopropane-1-CarboxylateSynthase,anEnzymeofEthyleneBiosynthesis 91 MałgorzataJakubowiczandWitoldNowak,AdamMickiewiczUniversity,Poznan,Poland 05 SpecificandNonspecificIncorporationofSeleniumintoMacromolecules 121 WilliamT.Self,UniversityofCentralFlorida,Orlando,FL,USA 06 ProteinToxinsfromBacteria 149 HolgerBarth,UniversityofUlmMedicalCenter,Ulm,Germany BradleyG.Stiles,WilsonCollege,Chambersburg,PA,USA;USArmyMedicalResearch InstituteofInfectiousDiseases,FortDetrick,MD,USA 07 HostDefensePeptides:BridgingAntimicrobialandImmunomodulatoryActivities 175 JasonKindrachuk,AnastasiaNijnik,andR.E.W.Hancock,UniversityofBritishColumbia, Vancouver,BC,Canada 08 BiosynthesisandModeofActionofLantibiotics 217 LisaE.Cooper,BoLi,andWilfredA.vanderDonk,UniversityofIllinoisatUrbana-Champaign, Urbana,IL,USA 09 PlantPeptideToxinsfromNonmarineEnvironments 257 Jan-ChristophWestermannandDavidJ.Craik,UniversityofQueensland,Brisbane,QLD,Australia 10 TherapeuticValueofPeptidesfromAnimalVenoms 287 NicolasAndreotti,BesmaJouirou,StephanieMouhat,LudovicMouhat,andJean-MarcSabatier, Universite´delaMe´diterrane´e–AmbriliaBiopharmaInc.,MarseilleCedex,France 11 SignalTransductioninGram-PositiveBacteriabyBacterialPeptides 305 IngolfF.Nes,OlaJohnsborg,andDzungBaoDiep,NorwegianUniversityofLifeSciences,Aas, Norway 12 ANewGenerationofArtificialEnzymes:CatalyticAntibodiesor‘Abzymes’ 323 Re´myRicouxandJean-PierreMahy,Universite´deParis-sud11,OrsayCedex,France 13 RecentProgressonUnderstandingRibosomalProteinSynthesis 353 UteKothe,UniversityofLethbridge,Lethbridge,AB,Canada 14 Glutaminyl-tRNAandAsparaginyl-tRNABiosyntheticPathways 383 JonathanL.Huot,JacquesLapointe,andRobertCheˆnevert,Universite´Laval,Que´bec,QC,Canada MarcBaillyandDanielKern,InstitutdeBiologieMole´culaireetCellulaire,Strasbourg,France 15 PosttranslationalModificationofProteins 433 KeithD.GreenandSylvieGarneau-Tsodikova,UniversityofMichigan,AnnArbor,MI,USA 16 CollagenFormationandStructure 469 HansPeterBa¨chinger,KazunoriMizuno,JaniceA.Vranka,andSergeiP.Boudko, OregonHealth&ScienceUniversity,Portland,OR,USA 17 LipidationofPeptidesandProteins 531 KristinaGo¨rmerandHerbertWaldmann,MaxPlanckInstituteofMolecularPhysiologyand TechnischeUniversita¨tDortmund,Dortmund,Germany LucBrunsveld,MaxPlanckInstituteofMolecularPhysiologyandChemicalGenomicsCentreofthe MaxPlanckSociety,Dortmund,Germany 18 GeneticIncorporationofUnnaturalAminoAcidsintoProteins 587 AngelaR.ParrishandLeiWang,TheSalkInstituteforBiologicalStudies,LaJolla,CA,USA 19 NonribosomalPeptideSynthetases 619 TimothyJ.MontavonandStevenD.Bruner,UniversityofFlorida,Gainesville,FL,USA 20 TheProperties,Formation,andBiologicalActivityof2,5-Diketopiperazines 657 P.J.MilneandG.Kilian,NelsonMandelaMetropolitanUniversity,PortElizabeth,SouthAfrica xii ContentsofallVolumes 21 Ubiquitin-DependentProteinDegradation 699 AshokN.Hegde,WakeForestUniversityHealthSciences,WinstonSalem,NC,USA Volume6 Carbohydrates,Nucleosides&NucleicAcids 01 OverviewandIntroduction 1 RobertWoodwardandPengGeorgeWang,TheOhioStateUniversity,Columbus,OH,USA 02 EnzymaticSynthesisofComplexCarbohydrates 5 WeiZhaoandTiehaiLi,NankaiUniversity,Tianjin,China RobertWoodward,ChengfengXia,andPengGeorgeWang,TheOhioStateUniversity, Columbus,OH,USA WanyiGuan,ShandongUniversity,Shandong,China 03 NewStrategiesforGlycopeptide,Neoglycopeptide,andGlycoproteinSynthesis 55 AshrafBrik,Ben-GurionUniversityoftheNegev,BeerSheva,Israel 04 CarbohydrateVaccines 91 QianliWangandZhongwuGuo,WayneStateUniversity,Detroit,MI,USA 05 MS-BasedGlycoanalysis 123 Kay-HooiKhoo,InstituteofBiologicalChemistry,AcademiaSinica,Taipei,Taiwan 06 GlycoanalysisofBacterialGlycome 157 ChuanWang,CamilleL.A.Hamula,andXing-FangLi,UniversityofAlberta,Edmonton,AB, Canada XinLiuandJianjunLi,NationalResearchCouncilofCanada,Ottawa,ON,Canada 07 ChemicalGlycobiology 175 ChadM.WhitmanandMichelleR.Bond,StanfordUniversity,Stanford,CA,USA JenniferJ.Kohler,UniversityofTexasSouthwesternMedicalCenter,Dallas,TX,USA 08 AlkaloidGlycosidaseInhibitors 225 AlanD.Elbein,UniversityofArkansasforMedicalSciences,LittleRock,AR,USA RussellJ.Molyneux,WesternRegionalResearchCenter,ARS-USDA,Albany,CA,USA 09 MolecularProbesforProteinGlycosylation 261 HowardC.Hang,TheRockefellerUniversity,NewYork,NY,USA 10 OAntigenBiosynthesis 297 MiguelA.Valvano,TheUniversityofWesternOntario,London,ON,Canada 11 BiosynthesisofComplexMucin-TypeO-Glycans 315 InkaBrockhausen,Queen’sUniversity,Kingston,ON,Canada 12 BacterialProteinGlycosylation 351 AmirrezaFaridmoayerandMarioF.Feldman,UniversityofAlberta,Edmonton,AB,Canada 13 StructureandBiosynthesisoftheMycobacterialCellWall 381 DeanC.Crick,DelphiChatterjee,MichaelS.Scherman,andMichaelR.McNeil, ColoradoStateUniversity,FortCollins,CO,USA 14 Structure,Biosynthesis,andFunctionofGlycosaminoglycans 407 CourtneyL.JonesandJianLiu,UniversityofNorthCarolina,ChapelHill,NC,USA DingXu,UniversityofCalifornia,SanDiego,CA,USA 15 BiochemistryandMolecularBiologyofGlycogenSynthesisinBacteriaandMammalsand StarchSynthesisinPlants 429 JackPreiss,MichiganStateUniversity,EastLansing,MI,USA 16 Celluloses 493 RajaiH.Atalla,CelluloseSciencesInternational,Madison,WI,USA AkiraIsogai,UniversityofTokyo,Tokyo,Japan ContentsofallVolumes xiii 17 VascularPlantLignification:Biochemical/StructuralBiologyConsiderationsofUpstream AromaticAminoAcidandMonolignolPathways 541 DhrubojyotiD.Laskar,OliverR.A.Corea,AnnM.Patten,ChulHeeKang, LaurenceB.Davin,andNormanG.Lewis,WashingtonStateUniversity,Pullman,WA,USA 18 Proanthocyanidins:ChemistryandBiology 605 DaneelFerreira,JannieP.J.Marais,ChristinaM.Coleman,andDesmondSlade, UniversityofMississippi,Oxford,MS,USA 19 NucleosideAnalogues 663 DarrellR.Davis,TheUniversityofUtah,SaltLakeCity,UT,USA 20 RNAModifyingEnzymes 683 GeorgeA.Garcia,JulieK.Hurt,andYi-ChenChen,UniversityofMichigan,AnnArbor,MI,USA 21 Riboswitches 743 TinaM.Henkin,TheOhioStateUniversity,Columbus,OH,USA Volume7 Cofactors 01 OverviewandIntroduction 1 TadhgP.Begley,TexasA&MUniversity,CollegeStation,TX,USA 02 RiboflavinBiosynthesis 3 MarkusFischer,UniversityofHamburg,Hamburg,Germany AdelbertBacher,TechnicalUniversityofMunich,Garching,Germany 03 Flavin-DependentEnzymes 37 RebeccaL.FaganandBruceA.Palfey,UniversityofMichiganMedicalSchool,AnnArbor,MI,USA 04 BiotechnologyofRiboflavinProduction 115 Hans-PeterHohmann,DSMNutritionalProducts,Kaiseraugst,Switzerland Klaus-PeterStahmann,FachhochschuleLausitz,Senftenberg,Germany 05 TheUseofSubsystemstoEncodeBiosynthesisofVitaminsandCofactors 141 AndreiL.Osterman,BurnhamInstituteforMedicalResearch,LaJolla,CA,USA RossOverbeek,FellowshipforInterpretationofGenomes,BurrRidge,IL,USA DmitryA.Rodionov,BurnhamInstituteforMedicalResearch,LaJolla,CA,USA 06 BiosynthesisofBiotin 161 Andre´eMarquet,Universite´PierreetMarieCurie,Paris,France 07 LipoicAcidBiosynthesisandEnzymology 181 ElizabethS.Billgren,RobertM.Cicchillo,NatashaM.Nesbitt,andSquireJ.Booker, ThePennsylvaniaStateUniversity,UniversityPark,PA,USA 08 GenomicsandEnzymologyofNADBiosynthesis 213 LeonardoSorci,OlegKurnasov,DmitryA.Rodionov,andAndreiL.Osterman, BurnhamInstituteforMedicalResearch,LaJolla,CA,USA 09 PyridoxalPhosphateBiosynthesis 259 JeremiahW.Hanes,StevenE.Ealick,andTadhgP.Begley,CornellUniversity,Ithaca,NY,USA IvoTews,HeidelbergUniversityBiochemistryCenter,Heidelberg,Germany 10 Pyridoxal59-Phosphate-DependentEnzymes:Catalysis,Conformation,andGenomics 273 SamantaRaboni,FrancescaSpyrakis,BarbaraCampanini,AlessioAmadasi,StefanoBettati, AlessioPeracchi,andAndreaMozzarelli,UniversityofParma,Parma,Italy;Presentaddress: UniversityofPadua,Padua,Italy RobertoContestabile,UniversityofRome‘LaSapienza,’Rome,Italy 11 CoenzymeABiosynthesisandEnzymology 351 ErickStrauss,StellenboschUniversity,Stellenbosch,SouthAfrica xiv ContentsofallVolumes 12 Menaquinone/UbiquinoneBiosynthesisandEnzymology 411 R.Meganathan,NorthernIllinoisUniversity,DeKalb,IL,USA 13 BiosynthesisofHemeandVitaminB 445 12 GunhildLayerandDieterJahn,TechnicalUniversityofBraunschweig,Braunschweig,Germany EvelyneDeery,AndrewD.Lawrence,andMartinJ.Warren,UniversityofKent,Kent,UK 14 CobalaminCoenzymesinEnzymology 501 PerryAllenFrey,UniversityofWisconsin-Madison,Madison,WI,USA 15 ThiaminBiosynthesis 547 TadhgP.BegleyandStevenE.Ealick,CornellUniversity,Ithaca,NY,USA 16 ThiaminEnzymology 561 FrankJordan,Rutgers,TheStateUniversityofNewJersey,Newark,NJ,USA 17 TheBiosynthesisofFolateandPterinsandTheirEnzymology 599 MarkusFischer,UniversityofHamburg,Hamburg,Germany BeatTho¨ny,UniversityChildren’sHospital,Zu¨rich,Switzerland SilkeLeimku¨hler,UniversityofPotsdam,Potsdam,Germany 18 CofactorCatabolism 649 TathagataMukherjee,KathrynM.McCulloch,StevenE.Ealick,andTadhgP.Begley, CornellUniversity,Ithaca,NY,USA 19 Protein-DerivedCofactors 675 VictorL.Davidson,UniversityofMississippiMedicalCenter,Jackson,MS,USA 20 BiosynthesisoftheMethanogenicCoenzymes 711 LauraL.GrochowskiandRobertH.White,VirginiaPolytechnicInstituteandStateUniversity, Blacksburg,VA,USA Volume8 EnzymesandEnzymeMechanisms 01 OverviewandIntroduction 1 ChristianP.Whitman,TheUniversityofTexas,Austin,TX,USA 02 EvolutionandtheEnzyme 9 ShelleyD.Copley,UniversityofColoradoatBoulder,Boulder,CO,USA 03 EnzymePromiscuity–EvolutionaryandMechanisticAspects 47 OlgaKhersonskyandDanS.Tawfik,WeizmannInstituteofScience,Rehovot,Israel 04 MechanisticandStructuralStudiesofMicrobialDehalogenases:HowNature CleavesaCarbon–HalogenBond 89 GerritJ.Poelarends,UniversityofGroningen,Groningen,TheNetherlands ChristianP.Whitman,TheUniversityofTexas,Austin,TX,USA 05 Guanidine-ModifyingEnzymesinthePenteinSuperfamily 125 ThomasW.LinskyandWalterFast,UniversityofTexas,Austin,TX,USA 06 TunnelsandIntermediatesintheGlutamine-DependentAmidotransferases 161 NigelG.J.Richards,RobertN.Humkey,KaiLi,andMeganE.Meyer,UniversityofFlorida, Gainesville,FL,USA TaniaC.Co´rdovadeSintjago,UniversidadCentraldeVenezuela,Caracas,Venezuela 07 FattyAcidBiosynthesisandOxidation 231 HuaningZhang,CarlA.Machutta,andPeterJ.Tonge,StonyBrookUniversity,StonyBrook, NY,USA 08 Diels–Alderases 277 HideakiOikawa,HokkaidoUniversity,Sapporo,Japan
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