Amino acids and peptides. Part 19. Synthesis of β-1- and β-2-adamantyl aspartates and their evaluation for peptide synthesis

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1、ViewArticleOnline/JournalHomepage/TableofContentsforthisissueJ.CHEM.SOC.PERKINTRANS.I19882129AminoAcidsandPeptides.Part19.'Synthesisofp-1-andp-2-AdamantylAspartatesandtheirEvaluationforPeptideSynthesistYoshioOkada*andShinlguchiFacultyofPharmaceuticalSciences,Kobe-GakuinUniversity,N

2、ishi-ku,Kobe673,Japanp-I-andP-2-Adamantylaspartates[H-Asp(0-I-Ada)-OHandH-Asp(O-2-Ada)-OH]havebeensynthesizedandtheirpropertiesexamined.Althoughthe1-AdagroupislabiletoTFA,the2-AdagroupisunaffectedduringTFAtreatment,buteasilyremovablebymethanesulphonicacid(MSA)atroomtemperaturewithi

3、n5min.Bothgroupsareunaffectedbytreatmentwith55%piperidineundercon-ditionswhicheasilycleavethefluoren-9-ylmethoxycarbonyl(Fmoc)groupfromana-aminogroup.Bothgroupscansuppressaspartimideformationasasidereactionunderacidicandbasicconditionsduringthesynthesisofaspartylpeptides.p-1-orp-2-

4、Adamantylaspartatesmaybeapplicabletosolid-phasepeptidesynthesisincombinationwithFmocorBocasanNa-protectinggroup,respectively.Somepropertiesoftheaspartimidemoietyaredescribed.Previously,wereportedthatthereactionbetweenBoc-aspartylpeptidewasexaminedbyh.p.1.c.AsshowninFigure1,Asp(OBz1

5、)-ONpandH-Ser-Ser-Thr-Ser-OMegaveBoc-theaspartimideringopenedgradually,togivea-orP-Asser-Ser-Thr-Ser-OMe(1)incrystallinepureformingoodaspartylpeptidecompletelyafter20hatroomtemperature.yieldwithasmallamountofthedesiredpentapeptide.*.$ThisAminoacidanalysesofacidandenzymichydrolysate

6、sofmajorsidereactionduringthesynthesisofpeptidescontainingH-Asp-Ser-Ser-Thr-Ser-OMe(3)andthepeptidederivedfromaspartylsequencessuchasAsp-Gly,Asp-Ser,andAsp-Hisis(2)in~/15phosphatebufferwerecarriedout.Inacidhydro-wellknown.3-6Theaspartimidemoietyopensundercertainlysatesofbothpeptide

7、s,theresultswereingoodagreementwithconditionstoformmainlyP-aspartylpeptide.'Itisverydifficultthetheoreticallyexpectedvalues.Incontrast,LAP(LeucinetoremoveeithertheaspartimidederivativeortheP-aspartyl-aminopeptidase;EC3.4.11.1)digests5*''gaveAsp:Thr:Serpeptidefromthedesiredpeptide.I

8、nordertosuppressthisside0: