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200513Vol.13,20056,529535ChineseJournalofSyntheticChemistryNo.6,5295353,,,,(,730000):,49:;;;:O623.7:A:100521511(2005)0620529207ApplicationofGuanidinesinMolecularRecognitionWUWen2jing,LURun2hua,GAOHai2xiang,CAOYu2juan,SHIYan2ping(LanzhouInstituteofChemicalPhysics,ChineseAcademyofSciences,Lanzhou730000,China)Abstract:Guanidineshavebeenrecognizedasoneofthemostpromisingreceptorsforvariousmolec2ularrecognition.Hereisasimpleintroductionabouttheirstructureandproperties.Themolecularrecognitionandprogressofmodifiedguanidinesinhost2guestchemistryweresummarizedwith49ref2erences.Keywords:guanidine;molecularrecognition;host2guestchemistry;review1861,,Streeker[1],DNA,,[2][3],[4],[5][6],,[7,8],20,,PKa,[9,10]PKa13.5[11],pH[12],,,,[13][1416],2090,[17,18][48][44],3:2004207208:(29873062):(1978-),,,,,E2mail:wuwenjing.licp@163.com:,Tel.028285243250,E2mail:lurh@cib.ac.cn;lurunhua@hotmail.com©1994-2009ChinaAcademicJournalElectronicPublishingHouse.Allrightsreserved.(),[3]CH6N+3,Scheme1NH2NH2ÝNH21aNÝH2H2NNH21bNH2H2NNÝH21cScheme1:,:(1),,,,[19],,[20];(2)[21],,6[22];(3)[23]2pH,,[12],[24,26],2.1206070,,,[12],:(1)N-H(Chart12a);(2)NH2(Chart12b);(3)N-H(Chart12c)Chart1Cotton[25,28],,,,-Jubian[27],(Scheme23b),(1),DNARNAScheme2035Vol.13,2005©1994-2009ChinaAcademicJournalElectronicPublishingHouse.Allrightsreserved.(30)26.500700Guanidine(20)24.500645Guanidine(10)17.000450Guanidine(5)11.000290RNA,Smith[28],RNA,,,RNA37,pH=7.05,820,Kurz[29],RNA,[30],RNA[19]:(1);(2);(3),Sasaki[31]ATP,1.7107mol-1Seel[32],,2.2DNADNA3[33]:;;DNA,,DNA,1996,BlaaskoA[34]DNA,DNA,DNARNAFukutomi[35],DNAATGC,,,,DNA,,2000,Barawkar[36]DNA,,,DNA,,,-,Onda[5],(),2.3,,,,1992,Galan[37](Chart2),,;,()()Chart2,Metzger[38],(3000),(40%e.e.)[39],1356:©1994-2009ChinaAcademicJournalElectronicPublishingHouse.Allrightsreserved.[40],,2.4(N-H+O-)Schmidtchen[41]X2NMR(5a,Chart3)(5b,Chart3),,,,,D,L222,D,L222D,L2Chart3,[42],2,,(Chart4),,2Table2Resultsoftheinteractionofguanidinederivativeswithnucleotidesandadipicacid(VV)1HNMRHabcdefD2O3.864.554.174.335.77.99D2O(CD3)2CO(41)3.124.443.984.245.848.16+D2O3.234.474.213.875.88.09+D2O(CD3)2CO(41)3.314.53.984.275.918.23+D2O(CD3)2CO(41)3.384.493.994.275.888.21D2O2.011.442.012.012.01D2O(CD3)2CO(41)2.31.53DMSO2.21.52+D2O2.071.43+D2O(CD3)2CO(41)2.071.44+D2O(CD3)2CO(41)2.281.55Chart42.5,1999,Nishizawa[43],(PPi),235Vol.13,2005©1994-2009ChinaAcademicJournalElectronicPublishingHouse.Allrightsreserved.(Scheme3)PPi,,[44],,[45][46],,,21,Scheme3[47],,,,,:(1),;(2),;(3);(4),,,,2.6,(),,,,[48](Scheme4),,,,,ZANAMIVIR[49](Chart5),,,Scheme4Chart5,-Na+(tetra2dotoxin)Na+,[2]3356:©1994-2009ChinaAcademicJournalElectronicPublishingHouse.Allrightsreserved.[1].[M].:,1994,(6):127-145.[2]RaczyskaED,CyraskiMK,GutowskiM,etal.Consequencesofprotontransferinguanidine[J].JPhysOrgChem,2003,16:91-106.[3]RiordanJF.Arginylresidesandanionbindingsitesinmolecular&cellularbiochemistry[J].Molecular&CellerBiochemistry,1979,26:71-92.[4]MinouxH,ChipotC.Cation2interactionsinpro2teins:cansimplemodelsprovideanaccuratedescrip2tion[J].JAmChemSoc,1999,121:10366-10372.[5]OndaM,YpshiharaK,KoyanoH,etal.Molecularrecognitionofnucleotidesbytheguanidiumunitatthesurfaceofaqueousmicellsandbilayers.Acomparisonofmicroscopicandmacroscopicinterface[J].JAmChemSoc,1996,118:8524-8530.[6]SchneiderSE,ONeilSN,AnslynEV.Couplingra2tionaldesignwithlibrariesleadstotheproductionofanATPselectivechemosensor[J].JAmChemSoc,2000,122:542-543.[7],,.[J].,1992,22:388-396.[8],,.[J].,2003,4:262-268.[9]DoctrichB,HnsseiniMW,LehnJM.Anionreceptormoleculessynthesisandanion-bindingpropertiesofpolyammonidmmacrocycles[J].JAmChemSoc,1981,103:1282.[10]KimuraE,KodamaM,YatsnnamiT.Macromonocy2clicpolyaminesasbiologicalpolyanioncomplexions.2.Ion2pairassociationwithphosphateandnucleo2tides[J].JAmChemSoc,1982,104:3182.[11]GobbiA,FrenkingG.Theequilibriumgeometriesandelectronicstructuresofguanidine,guanidiniumcation,urea,and1,12diaminoethylene[J].JAmChemSoc,1993,115:2362-2372.[12]EchavarrenA,GalanA.Chiralrecognitionofaro2maticcarboxylateanionsbyanopticallyactiveabioticreceptorcontainingarigidguanidiniumbindingsub2unit[J].JAmChemSoc,1989,111:4994-4995.[13]IshikawaT,IsobeT.Modifiedguanidinesaschiralauxiliaryies[J].ChemEurJ,2002,8:552-557.[14]SimoniD,InvidiataPF,ManfrediniS,etal.Facilesynthesisof22nitroalkanolsbytetramethylguanidine(TMG)2catalyzedadditionofprimarynitroalkanestoalicyclicketones[J].TetrahedronLetters,1997,38:2749-2752.[15]SimoniD,InvidiataPF,ManfrediniS,etal.Tetra2methylguanidine(TMG)2catalyzedadditionofdialkylphosphatesto,2unsaturatedcarbonylcompounds,alkenenitriles,aldehydes,retonesandimines[J].TetrahedronLetters,1998,39:7615-7618.[16]SimoniD,RondaninR,MassimoM,etal.1,5,72Triazabicyclo[4.4.0]dec212ene(TBD),72methyl2TBD(MTBD)andthepolymer2supportedTBD(P2TBD):threeefficientcatalystsforthenitroaldol(Henry)reactionand