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1、EarlystudiesrevealedthatLprolinecouldcatalyzethedirectaldolreactionbutinmanycaseobtainingracemicproductinaqueousmedium.MeoverconsideringthatGolefesgroupreptedtheDNAbasedasymmetriccatalysisDNAcouldinteractwithaminoacidsth
2、roughHbondwhichwasconstituentpartofproteinrecognizedasthesmallestproteininasymmetriccatalysis.WeassumethattheenantioivitycouldbeimprovedifthistypeofchiralacidservedasanadditiveintheLprolinecatalyzedaldolreactionsduetoaco
3、operativeeffectinthecatalyticsystem(Scheme1).InthispaperwereptanimprovedLprolinecatalyzedaldolreactioninaqueousmedium.Undertheoptimizedconditionsthealdolproductwasaffdedinupto53%inaqueousmedium.OOHCNO2OOHNO2DNALprolineH2
4、O40vol%Scheme1Table1TheAldolreactioncatalyzedbyDNAprolineinwaterEntryDNAproline(mmol)bYield%Ee%10.0389.7Rac.20.03212730.06263340.12243250.243828Reactionconditions:DNA:10mg4nitrobenzaldehyde:0.1mmolH2O:1.5mlacetone:1.5mlr
5、tf5d.a:noDNA.b:moleoftheproline.Table2TheeffectofwaterintheeeftheDNAprolinecatalyzedaldolreactionofacetonewith4nitrobenzaldehydeEntryH2O%Yield%Ee%Ee%a10767065225605393402342Rac.4502633Rac.5662834Rac.6751611Rac.Reactionco
6、nditions:DNA:10mgLproline:0.06mmol4nitrobenzaldehyde:0.1mmolrtf5d.a:noDNATheeffectofwateracetoneratioontheenantiomericexcessoftheproductwasalsoinvestigated(Table2).Thelowereesomuchasracemicproductwasobtainedinthepresence
7、ofwatercatalyzedbyLprolineonlyhoweverinthepresenceofDNAitwasobtainedenantioiveproduct.Theeewasfrom53%to11%accompanyingwiththeratioofwaterfrom25%to75%(entry26).InganicmediumthepresenceofDNAcouldalsoincreasetheeefrom65%to7
8、0%.ItwasdemonstratedthatDNAplayedanimptantroleinthealdolreactioninaqueousmedium.9LLys874Reactionconditions:DNA:10mgaminoacid:0.06mmol4nitrobenzaldehyde:0.1mmolH2O:1.0mlacetone:1.5mlrtf5dThecatalyticabilityofotheraminoaci
9、dwasalsoinvestigated(Table6).Theacidicneutralaminoacidgavebetterresultthanthatofbasicaminoacid(entry136vs79)whichgavebetterreactionrate.BecauseofinteractionofDNAwithaminoacidthroughHbondtightlytheactivecentreoftheaminoac
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