Tetrapyrroles: Birth, Life and Death PDF
Preview Tetrapyrroles: Birth, Life and Death
MOLECULAR BIOWGY INTEUlGENCE UNIT Tetrapyrroles Birth, Life and Death J. Martin Warren, PhD Protein Science Group Department ofBiosciences UniversityofKent Canterbury, Kent, UK Alison G. Smith, PhD Department ofPlantSciences UniversityofCambridge Cambridge, UK LANDES BIOSCIENCE SPRINGERScIENCE+BuSINESSMEDIA AUSTIN, TEXAS NEW YORK,NEWYORK USA USA TETRAPYRROLES: BIlITH, LIFE AND DEATH MolecularBiologyIntelligenceUnit LandesBioscience SpringerScience+BusinessMedia,LLC ISBN:978-0-387-78517-2 Printedonacid-freepaper. Copyright©2009LandesBioscienceandSpringerScience+BusinessMedia,LLC All rights reserved. This work may not be translated or copied in whole or in part without the written permissionofthepublisher,exceptforbriefexcerptsinconnectionwithreviewsorscholarlyanalysis.Usein connectionwithanyformofinformationstorageandretrieval,electronicadaptation,computersoftware,or bysimilarordissimilarmethodologynowknownorhereafterdevelopedisforbidden. Theuseinthepublicationoftradenames,trademarks,servicemarksandsimilartermseveniftheyarenot identifiedassuch, is not to be taken as an expressionofopinionas towhetheror not theyaresubjectto proprietaryrights. Whiletheauthors,editorsandpublisherbelievethatdrugselectionanddosageand thespecificationsand usageofequipmentanddevices,assetforth inthisbook,areinaccordwithcurrentrecommendationsand practiceatthe timeofpublication, theymake nowarranty,expressedorimplied,with respectto material describedin this book. Inviewoftheongoingresearch, equipmentdevelopment,changesingovernmental regulationsandtherapidaccumulationofinformationrelatingtothebiomedicalsciences,thereaderisurgedto carefuUyreviewandevaluatetheinformationprovidedherein. SpringerScience+BusinessMedia,LLC,233SpringStreet,NewYork,NewYork10013,USA http://www.springer.com PleaseaddressallinquiriestothePublishers: LandesBioscience,1002WesrAvenue,Austin,Texas78701,USA Phone:512/6376050;FAX:512/6376079 http://www.landesbioscience.com PrintedintheUnitedStatesofAmerica. 9 876 5 4 3 2 1 LibraryofCongressCataloging-in-PublicationData J. Tetrapyrroles: birth,life, anddeath IeditedbyMartin Warren,AlisonG. Smith. p. icm. Includesbibliographical referencesandindex. ISBN 978-0-387-78517-2 (alk. paper) J. 1. Tetrapyrroles.2. Chlorophyll. 3. Porphyrins.4. Heme. I.Warren, Martin II. Smith,AlisonG. [DNLM: 1. Tetrapyrroles. QD401 T348 2009] QP670.T482009 572'.46--dc22 2008005850 About the Editors... J" MARTIN WARREN, PhD,isProfessorofBiochemistryattheUniversity ofKent, Canterbury, UK. For the past twenty years he has studied tetrapyrrole biosynthesis,includingthesynthesisofthemacrocyclicringstructureanditstrans formation into heme, sirohemeandvitamin BIZ" He has recently been awardeda Biotechnology and Biological Science Research Council (BBSRC) professional fellowship to continue his work on metabolic engineering ofcomplex biosyn theticpathways.HereceivedhisPhDfrom theUniversityofSouthampton,Hants, UK, and did his postdoctoral workatTexasA&M, CollegeStation,Texas, USA. About the Editors... ALISON SMITH, PhD, is ProfessorofPlant Biochemistryin the Depart ment ofPlant Sciences, University ofCambridge, UK. She obtained a BSc in Biochemistry from the University ofBristol, and a PhD in Plant Biochemistry fromtheUniversityofCambridge.Herresearchisfocusedonmetabolisminplants, microbes and algae, in particular that for tetrapyrrole biosynthesis and vitamin metabolism. Sheisknown forherworkontheidentificationandcharacterisation oftheenzymesinvolvedinhaembiosynthesisinhigherplantsandindetermining the subcellular location and regulation ofthe pathway. More recently, she was instrumental in establishing the widespread interaction in which algae obtain vitaminB from bacteriainexchangefor fixed carbon. t2 CONTENTS r;::::::============= ================;-] Preface xv 1. An HistoricalIntroductionto PorphyrinandChlorophyllSynthesis .....1 MichaelR. Moore Historical Introduction to Porphyrinsand Porphyrias 1 Structure 4 TheEarlyChemical Era 9 The Biochemical DescriptiveEra 10 EarlyDescriptionofPorphyria 11 ClassificationofPorphyrias 12 Enzymes 14 Acute Porphyria 15 Nonacute Porphyrias 17 PorphyriainAnimals 18 PorphyrinSynthesisin theAnimal Kingdom 19 The HarderianGland 19 Phototherapyand Cancer 19 Retrospective Diagnoses 20 Ephemera: Porphyrinurias 21 2. Biosynthesisof5-AminolevulinicAcid 29 DieterJahn andDirkW Heinz CondensationofSuccinyl-CoAand Glycine intoAminolevulinicAcid 29 TransferRNA-DependentAminolevulinicAcid Formation 30 3. 5-AminolaevulinicAcid Dehydratase, Porphobilinogen Deaminase andUroporphyrinogenIIISynthase 43 HeidiL. Schubert, Peter T ErskineandJonathan B. Cooper 5-AminolaevulinicAcid Dehydratase 43 Porphobilinogen Deaminase 58 Uroporphyrinogen IIISynthase 61 4. TransformationofUroporphyrinogenIIIintoProtohaem 74 JohannaE. CornahandAlison G. Smith Uroporphyrinogen III Decarboxylase 76 CoproporphyrinogenIIIOxidase/Dehydrogenase 77 Protoporphyrinogen IXOxidase 79 Ferrochelatase 81 OrganizationofPathway 82 5. InheritedDisordersofHaemSynthesis:TheHuman Porphyrias 89 MichaelN BadmintonandGeorgeH. Elder Overview 89 MolecularGeneticsand Pathogenesis 93 MechanismsofDisease 96 NewApproaches to Management 97 6. HemeDegradation: MechanisticandPhysiologicalImplications 101 Angela Wilks Evolutionand Biological FunctionofHemeOxygenase 101 SequenceandStructuralConservationwithinthe Heme OxygenaseEnzymes , 103 CrystallographicStudies 103 Mechanism ofHemeOxygenase 107 BiliverdinReduction to Bilirubin 110 BiliverdinIXaReductase 110 BiliverdinIXf3Reductase 113 7. RegulationofMammalianHemeBiosynthesis 116 AmyE. MedlockandHarryA. Dailey RegulationofHemeBiosynthesisbyALASynthase 117 RegulationatSitesOtherThanALAS 121 8. TetrapyrrolesinPhotodynamicTherapy 128 DavidI VernonandIan Walker BriefHistory 128 SingletOxygen:TheCytotoxicAgent 129 SingletOxygenTargets 129 LightDeliveryand Requirement 130 PhotodynamicDamage 130 MechanismsofTumourandCellularUptake 131 TetrapyrrolesinPhotodynamicTherapy 131 HaematoporphyrinDerivative(HpD) and Photofrin 131 TheIdeal PropertiesofaPhotosensitiser 132 SecondGenerationPhotosensitisers 133 5,10,15,20Tetrakis (meso-hydroxyphenyl) Chlorin (m-THPC, Foscan, temoporfin) 133 5,10,15,20Tetrakis (meso-hydroxyphenyl) Bacteriochlorin (m-THPBC) 134 BenzoporphyrinDerivative (BPD,Verteporfin) 135 TinEthylEtiopurpurin (SnEt2, Purlytin, Rostaporfin) 136 Mono-L-AspartylChlorine6 (Npe6, MACE,Talaporfin) 136 Palladium-Bacteriopheophorbide(TOOKAD,WST009) 137 2-[1-hexyloxyethyl]-2-DevinylPyropheophorbide-a (HPPH, Photochlor) 138 Phthalocyanines 139 LutetiumTexaphyrin (Lu-tex,MotexafinLutetium) 139 5-AminolaevulinicAcid 140 ClinicalALA-PDT 141 OtherApplicationsofALA-PDT 141 AminolaevuJinicAcid Esters 141 PhotodetectionofTumours 142 9. HemeTransportandIncorporationintoProteins 149 Linda Thony-Meyer LocalizationofHemein Prokaryotes 150 Bacterial HemeTransport 151 HemeTransportinEukaryotes 153 Unassisted HemeTransport 155 Heme-ProteinAssembly 155 10. HemeandHemoproteins 160 AndrewW Munro, HazelM. Girvan, Kirstyj. McLean, MylesR. CheesmanandDavidLeys TheHemeSyntheticPathway 160 StructuralVariationsofthe HemeCofactor 162 HemeIronCoordinationin Hemoproteins 165 DiversityofHemoprotein Form and Function 168 SpectroscopicAnalysisofHemoproteins 171 NovelAspectsand FutureProspects 175 11. Novel Heme-ProteinInteractions-SomeMoreRadical ThanOthers 184 AnnSmith HemeasaSensor: InteractionsofHemewith Proteins ThatLead to RecognitionofGaseousMolecules: Oxygen, CarbonMonoxideand NitricOxide 186 HemeBindingto IonChannels.. 187 Novel Low-Spin Heme-Protein Interactions 188 Heme-BindingProteinsThatAre Protective, Preventing Heme-MediatedOxidativeStress 189 HemeTransportacross Enterocyresand ProofofPrinciple 193 InteractionsofHemewithTranscription Factors 195 Heme-Protein Interactionsand the Control ofCircadian Rhythms 196 Novel Heme-ProteinInteractionsfor the Control ofIntracellularHemeLevels 199 RelationshipsbetweenATPConcentrations, OxygenTension and HemeTransporters, ManyofWhichAlso Interact with Porphyrins 201 12. Synthesisand RoleofBilinsinPhotosyntheticOrganisms 208 NicoleFrankenberg-DinkelandMatthewj. Terry StructureandSpectral PropertiesofProtein-Bound Bilins 208 SynthesisofBiliverdin IXubyHemeOxygenases 210 BiosynthesisofBilinsbyFerredoxin-Dependent Bilin Reductases 212 AssemblyofPhycobiliproteinsand Phyrochromes 216 The RolesofBilinsin PhotosyntheticOrganisms 216 13. Phytochromes: Bilin-LinkedPhotoreceptorsinBacteriaandPlants...221 Matthew]. TerryandAlexC. McCormac ThePhytochromes-ADiverseFamilyofPhotoreversible Photoreceptors 222 PhytochromePhotosensoryDomains 224 Physiological Rolesofphytochrome-LikeProteinsinProkaryotes 226 PhytochromeFunctioninFloweringPlants 227 SpecificRolesforSpecificPhytochromes 227 PhytochromeModeofAction 229 PhytochromeRegulationofTetrapyrroleSynthesis 229 14. BiosynthesisofChlorophyllandBacteriochlorophyll 235 Derren]. HeyesandC. NeilHunter TheInsertionoftheCentralMagnesium Ion 237 MethylationofRingC 238 TheMissingLinkinChlorophyllBiosynthesis:TheFormation oftheIsocyclicRingEofProtochlorophyllide 239 Reductionofthe8-VinylGroup 240 TwoRoutesfor the ReductionofPchlide 241 POR:ALight-DrivenEnzyme 241 DPOR:AMulti-SubunitEnzyme 243 TheStepsUnique to BacteriochlorophyllBiosynthesis 244 TheFinalSteps:Additionand Reductionofthe PhytolTail 245 15. RegulationofTetrapyrroleSynthesisinHigherPlants 250 Matthew]. TerryandAlisonG. Smith Regulationofthe PlantTetrapyrrolePathway-Atthe Heart ofPlantMetabolism? 252 TurningontheTap-RegulationoftheSynthesisofthe Initial Precursor,ALA 253 DecisionTimeatthe Branchpoints 256 RegulationoftheChlorophyll Branch 258 16. RegulationoftheLateStepsofChlorophyllBiosynthesis 263 WolfhartRudiger LightRegulationviaNADPH: Protochlorophyllide Oxidoreductase(POR) 264 RegulationofChlorophyllbBiosynthesis 267 ANew Role forCarotenoids? 269 17. ChlorophyllBreakdown 274 BernhardKrautler ChlorophyllBreakdowninHigher Plants 274 EarlySteps 275 CleavageoftheChlorophyllMacroring 276 TheArrivalatColorlessandNonfluorescentChlorophyll BreakdownProducts 278 Breakdown BeyondtheStageofColorlessTetrapyrtolicCatabolites 280 ChlorophyllCatabolitesfrom OtherSources 282 18. Vitamin B12: Biosynthesisofthe CorrinRing 286 RossM. Graham, EvelyneDeeryandMartinJ Warren The FirstCommonStep: ProductionofPrecorrin-2 287 TheAerobicPathway 288 ProductionofHydrogenobyrinicAcid 291 ProteinsofUnknown Function 293 TheAnaerobic Pathway 293 ProductionofCobait-Precorrin-6A 295 19. ConversionofCobinamideintoCoenzymeB 300 12 Jorge C. Escalante-Semerena,JesseD. Woodson, NicoleR. Buan andCarmen L. Zayas Attachmentof5-Deoxyadenosine, the Upper (CofJ) Ligand ofCoenzymeB 300 12 The NucleotideLoopAssembly (NLA) Pathway 304 20. TheRegulationofCobalaminBiosynthesis 317 Jeffrey G. Lawrence TheComplexityofCobalamin 317 CobalamininContext: RegulatingaBranch Point 319 Operon Inductionand Physiological Significance 321 Operon Repressionand mRNABinding 323 TheSynergyofCobalaminTransportandSynthesis 324 21. CoenzymeB -CatalyzedRadical Isomerizations 330 12 DominiquePadovaniandRumaBanerjee StructuralInsightsinto the B -Dependent Isomerases 331 12 Co-CBondActivationinB -Dependent Isomerases 333 12 Radical Flights: ConformationalChangesat Play 336 Rearrangement ReactionsCatalyzedbyB -Dependent Enzymes 338 12 22. BiosynthesisofSirohemeandCoenzymeF430 343 MartinJ Warren, EvelyneDeeryandRuth-SarahRose Siroheme Biosynthesis 343 CoenzymeF430 Biosynthesis 346 23. RoleofCoenzymeF inMethanogenesis 352 430 EvertC. Duin Methanogenesis 353 FreeFactor430 354 NameThatSignal 355 EPRSignalsinWholeCells 358 StructureofMCRandtheNickel Site 360 OxidationStateofNickel in the MCRoxl Form 362 Activationand InactivationofMethyl-CoenzymeM Reductase 363 Preludeto theCatalyticMechanism 366 CatalyticMechanism 367 AnaerobicCH4Oxidation 370 MCRIsStillaMystery 370 24. TheRoleofSirohemeinSulfiteandNitriteReducuses 375 M ElizabethStroupeandElizabethD. Getzoff Siroheme-ContainingSulfiteandNitriteReductasesRepresent aSingleEnzymeClass 375 DiversirybetweentheSiRandNiREnzymes 377 SymmetryDefinesHomologybetweentheAssimilatory and DissimilatoryEnzymes 378 SiRsand NiRs Have MultipleRedoxCentersandIntricate SpectroscopicFeatures 378 X-RayCrystallographicStructuresSupporttheSpectroscopicData 378 SirohemeIsatthe HeartoftheSix-Electron ReductionofSulfite toSulfideorNitritetoAmmonia 379 SirohemeAnchors theTransformationofSulfitetoSulfide orNitrite toAmmonia 381 TheSirohemeTerrapyrroleShowsSignificantDeparture from Planariry 382 Siroheme'sStructuralandElectronicCharacteristicsControl Anion Interactions 386 APossible3tCation Radical Intermediate 387 25. TheRoleofHemed inDenitrification 390 1 Stuart]. Ferguson StructureofCytochromec~ 391 MechanismofNitriteReduction 394 Insightsintod] hemeChemistryfrom ModelCompoundStudies 395 Biosynthesisofd] heme 396 Index 401
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