Schomburg · Schomburg Editors springsperringer regnirps HandbHoaonkd book koobdnaH of of fo regnirps regnirps EnzymEenszymes semyznE REGNIRPS koobdnaH S P SRPIRNINGGERER koobdnaH 2nd Editi2onnd Edition noitidE dfno2 fo semyznE semyznE REGNIRPS SPRINGER REGNIRPS H Hanadnbdobookok koobdnaH noitidE dn2 noitidE dn2 1 1 1 koofbod n a H H a n d o b f oofok n koobdnaH o i 1 t 1 i semyznE E nEznyzmymeses d fo of fo tnemelppus tnemelppus supplesmuepnptl ement supplemsuenpptl ement E 8s emulov 8s emulov volumev os8lume s8 volumev os8lume s8 d n semyznE Enzymes o semyznE tnemelppus tnemelppus supplement c tnemelppus tnemelppus e 8s e1m suslaolvc 8s e1m suslaolvc class 1class 1 vcloalussm 1ec lsa8ss 1 S 8s emulov 8s emulov OxidOorxeiddourcetdasuecstases sesatcuderodixO OxidoO xido odixO 1 ss1a clce sesa1tc susdalecr reductraesdeusctases cecla 1ss 1ec 1 1 ssalc 1 ssalc sesatcuderodixO odi1x cOe ec 1 ec 1 Oxidoreductases sesatcuderodixO odixO 1 ce sesatcuder ec 1 1 ce sesatcuder 1 ce 1 ce 123 Springer Handbook of Enzymes Supplement Volume S8 Dietmar Schomburg and Ida Schomburg (Eds.) Springer Handbook of Enzymes Supplement Volume S8 Class 1 Oxidoreductases EC 1 coedited by Antje Chang Second Edition 1 3 Professor Dietmar Schomburg TechnicalUniversityBraunschweig e-mail: [email protected] Bioinformatics & Systems Biology Langer Kamp 19b Dr. Ida Schomburg 38106 Braunschweig e-mail: [email protected] Germany Dr. Antje Chang e-mail: [email protected] Library of Congress Control Number: 2013933107 ISBN 978-3-642-36264-4 ISBN (eBook) 978-3-642-36265-1 2nd Edition Springer Berlin Heidelberg New York The first edition was published as the “Enzyme Handbook, edited by D. and I.Schomburg”. Thisworkissubjecttocopyright.Allrightsarereserved,whetherthewholeorpartofthematerialis concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting,reproductiononmicrofilmorinanyotherway,andstorageindatabanks.Duplication ofthispublicationorpartsthereofispermittedonlyundertheprovisionsoftheGermanCopyright LawofSeptember9,1965,initscurrentversion,andpermissionforusemustalwaysbeobtained fromSpringer.ViolationsareliabletoprosecutionundertheGermanCopyrightLaw. SpringerisapartofSpringerScience+BusinessMedia springer.com #Springer-VerlagBerlinHeidelberg2013 PrintedinGermany Theuseofgeneraldescriptivenames,registerednames,etc.inthispublicationdoesnotimply,even intheabsenceofaspecificstatement,thatsuchnamesareexemptfromtherelevantprotectivelaws andregulationsandfreeforgeneraluse. Thepublishercannotassumeanylegalresponsibilityforgivendata,especiallyasfarasdirectionsfor theuseandthehandlingofchemicalsandbiologicalmaterialareconcerned.Thisinformationcanbe obtainedfromtheinstructionsonsafelaboratorypracticeandfromthemanufacturersofchemicals andlaboratoryequipment. Coverdesign:ErichKirchner,Heidelberg Typesetting:medionetPublishingServicesLtd.,Berlin Printedonacid-freepaper 2/3141m-543210 Preface Today, as the full information about the genome is becoming available for a rapidly increasing number of organisms and transcriptome and proteome analysesarebeginningtoprovideuswithamuchwiderimageofproteinregu- lationandfunction,itisobviousthattherearelimitationstoourabilitytoaccess functionaldata for the geneproducts –theproteinsand,inparticular,foren- zymes. Those data are inherently very difficult to collect, interpret and stan- dardizeastheyarewidelydistributedamongjournalsfromdifferentfieldsand areoftensubjectto experimentalconditions.Nevertheless asystematiccollec- tionisessentialforourinterpretationofgenomeinformationandmoresofor applicationsofthisknowledgeinthefieldsofmedicine,agriculture,etc.Progress onenzymeimmobilisation,enzymeproduction,enzymeinhibition,coenzyme regenerationandenzymeengineeringhasopenedupfascinatingnewfieldsfor thepotentialapplicationofenzymesinawiderangeofdifferentareas. ThedevelopmentoftheenzymedatainformationsystemBRENDAwasstartedin 1987 at the German National Research Centre for Biotechnology in Braun- schweig(GBF),continuedattheUniversityofColognefrom1996to2007,and then returned to Braunschweig, to the Technical University, Institute of Bio- informatics & Systems Biology. The present book “Springer Handbookof En- zymes”representstheprintedversionofthisdatabank.Theinformationsystem hasbeendevelopedintoafullmetabolicdatabase. The enzymes in this Handbook are arranged according to the Enzyme Com- mission list of enzymes. Some 5,000 “different” enzymes are covered. Fre- quently enzymes with very different properties are included under the same EC-number.Althoughweintendtogivearepresentativeoverviewonthechar- acteristicsandvariabilityofeachenzyme,theHandbookisnotacompendium. Thereaderwillhavetogototheprimaryliteratureformoredetailedinforma- tion.Naturallyit isnotpossibletocoverallthenumerousliteraturereferences foreachenzyme(forsomeenzymesupto40,000)ifthedatarepresentationisto beconciseasisintended. Itshouldbementionedherethatthedatahavebeenextractedfromtheliterature andcriticallyevaluatedbyqualifiedscientists.Ontheotherhand,theoriginal authors’ nomenclatureforenzyme formsand subunits is retained. Inorder to keepthetablesconcise,redundantinformationisavoidedasfaraspossible(e.g. if K values are measured inthe presence of an obvious cosubstrate, only the m nameofthecosubstrateisgiveninparenthesesasacommentarywithoutrefer- encetoitsspecificrole). Theauthorsaregratefultothefollowingbiologistsandchemistsforinvaluable helpinthecompilationofdata:CorneliaMunarettoandDr.AntjeChang. Braunschweig Autumn2012 DietmarSchomburg,IdaSchomburg V List of Abbreviations A adenine Ac acetyl ADP adenosine5’-diphosphate Ala alanine All allose Alt altrose AMP adenosine5’-monophosphate Ara arabinose Arg arginine Asn asparagine Asp asparticacid ATP adenosine5’-triphosphate Bicine N,N’-bis(2-hydroxyethyl)glycine C cytosine cal calorie CDP cytidine5’-diphosphate CDTA trans-1,2-diaminocyclohexane-N,N,N,N-tetraaceticacid CMP cytidine5’-monophosphate CoA coenzymeA CTP cytidine5’-triphosphate Cys cysteine d deoxy- d- (andl-)prefixesindicatingconfiguration DFP diisopropylfluorophosphate DNA deoxyribonucleicacid DPN diphosphopyridiniumnucleotide(nowNAD+) DTNB 5,5’-dithiobis(2-nitrobenzoate) DTT dithiothreitol(i.e.Cleland’sreagent) EC numberofenzymeinEnzymeCommission’ssystem E.coli Escherichiacoli EDTA ethylenediaminetetraacetate EGTA ethyleneglycolbis(-aminoethylether)tetraacetate ER endoplasmicreticulum Et ethyl EXAFS extendedX-rayabsorptionfinestructure FAD flavin-adeninedinucleotide FMN flavinmononucleotide(riboflavin5’-monophosphate) Fru fructose Fuc fucose G guanine Gal galactose VII ListofAbbreviations GDP guanosine5’-diphosphate Glc glucose GlcN glucosamine GlcNAc N-acetylglucosamine Gln glutamine Glu glutamicacid Gly glycine GMP guanosine5’-monophosphate GSH glutathione GSSG oxidizedglutathione GTP guanosine5’-triphosphate Gul gulose h hour H4 tetrahydro HEPES 4-(2-hydroxyethyl)-1-piperazineethanesulfonicacid His histidine HPLC highperformanceliquidchromatography Hyl hydroxylysine Hyp hydroxyproline IAA iodoacetamide IC50 50%inhibitoryconcentration Ig immunoglobulin Ile isoleucine Ido idose IDP inosine5’-diphosphate IMP inosine5’-monophosphate ITP inosine5’-triphosphate K Michaelisconstant m l- (andd-)prefixesindicatingconfiguration Leu leucine Lys lysine Lyx lyxose M mol/l mM millimol/l m- meta- Man mannose MES 2-(N-morpholino)ethanesulfonate Met methionine min minute MOPS 3-(N-morpholino)propanesulfonate Mur muramicacid MW molecularweight NAD+ nicotinamide-adeninedinucleotide NADH reducedNAD NADP+ NADphosphate NADPH reducedNADP NAD(P)H indicateseitherNADHorNADPH VIII ListofAbbreviations NBS N-bromosuccinimide NDP nucleoside5’-diphosphate NEM N-ethylmaleimide Neu neuraminicacid NMN nicotinamidemononucleotide NMP nucleoside5’-monophosphate NTP nucleoside5’-triphosphate o- ortho- Orn ornithine p- para- PBS phosphate-bufferedsaline PCMB p-chloromercuribenzoate PEP phosphoenolpyruvate pH -log10[H+] Ph phenyl Phe phenylalanine PHMB p-hydroxymercuribenzoate PIXE proton-inducedX-rayemission PMSF phenylmethane-sulfonylfluoride p-NPP p-nitrophenylphosphate Pro proline (cid:2) Q factorforthechangeinreactionratefora10 Ctemperatureincrease 10 Rha rhamnose Rib ribose RNA ribonucleicacid mRNA messengerRNA rRNA ribosomalRNA tRNA transferRNA Sar N-methylglycine(sarcosine) SDS-PAGE sodiumdodecylsulfatepolyacrylamidegelelectrophoresis Ser serine T thymine t timeforhalf-completionofreaction H Tal talose TDP thymidine5’-diphosphate TEA triethanolamine Thr threonine TLCK Na-p-tosyl-l-lysinechloromethylketone T meltingtemperature m TMP thymidine5’-monophosphate Tos- tosyl-(p-toluenesulfonyl-) TPN triphosphopyridiniumnucleotide(nowNADP+) Tris tris(hydroxymethyl)-aminomethane Trp tryptophan TTP thymidine5’-triphosphate Tyr tyrosine U uridine IX