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dc.contributor.authorInokuchi, Erikoja
dc.contributor.authorYamada, Aija
dc.contributor.authorHozumi, Kentaroja
dc.contributor.authorTomita, Kenjija
dc.contributor.authorOishi, Shinyaja
dc.contributor.authorOhno, Hiroakija
dc.contributor.authorNomizu, Motoyoshija
dc.contributor.authorFujii, Nobutakaja
dc.contributor.alternative大石, 真也ja
dc.contributor.alternative藤井, 信孝ja
dc.date.accessioned2012-06-28T07:31:42Z-
dc.date.available2012-06-28T07:31:42Z-
dc.date.issued2011-05-07ja
dc.identifier.issn1477-0520ja
dc.identifier.urihttp://hdl.handle.net/2433/156967-
dc.description.abstractAmidine-type peptide bond isosteres were designed based on the substitution of the peptide bond carbonyl (C=O) group with an imino (C=NH) group. The positively-charged property of the isosteric part resembles a reduced amide-type peptidomimetic. The peptidyl amidine units were synthesized by the reduction of a key amidoxime (N-hydroxyamidine) precursor, which was prepared from nitrile oxide components as an aminoacyl or peptidyl equivalent. This nitrile oxide-mediated C-N bond formation was also used for peptide macrocyclization, in which the amidoxime group was converted to peptide bonds under mild acidic conditions. Syntheses of the cyclic RGD peptide and a peptidomimetic using both approaches, and their inhibitory activity against integrin-mediated cell attachment, are presented.ja
dc.format.mimetypeapplication/pdfja
dc.language.isoengja
dc.publisherRoyal Society of Chemistryja
dc.rights© The Royal Society of Chemistry 2011ja
dc.rightsThis is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。ja
dc.subject.meshAmidines/chemistryja
dc.subject.meshAmino Acids/chemistryja
dc.subject.meshDrug Designja
dc.subject.meshEsters/chemistryja
dc.subject.meshIons/chemistryja
dc.subject.meshMolecular Structureja
dc.subject.meshNitriles/chemistryja
dc.subject.meshOxides/chemistryja
dc.subject.meshPeptides/chemical synthesisja
dc.subject.meshPeptidomimetics/chemical synthesisja
dc.titleDesign and synthesis of amidine-type peptide bond isosteres: application of nitrile oxide derivatives as active ester equivalents in peptide and peptidomimetics synthesis.ja
dc.type.niitypeJournal Articleja
dc.identifier.ncidAA1168650Xja
dc.identifier.jtitleOrganic & biomolecular chemistryja
dc.identifier.volume9ja
dc.identifier.issue9ja
dc.identifier.spage3421ja
dc.identifier.epage3427ja
dc.relation.doi10.1039/c0ob01193bja
dc.textversionauthorja
dc.identifier.pmid21423919ja
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