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dc.contributor.author | Inokuchi, Eriko | en |
dc.contributor.author | Yamada, Ai | en |
dc.contributor.author | Hozumi, Kentaro | en |
dc.contributor.author | Tomita, Kenji | en |
dc.contributor.author | Oishi, Shinya | en |
dc.contributor.author | Ohno, Hiroaki | en |
dc.contributor.author | Nomizu, Motoyoshi | en |
dc.contributor.author | Fujii, Nobutaka | en |
dc.contributor.alternative | 大石, 真也 | ja |
dc.contributor.alternative | 藤井, 信孝 | ja |
dc.date.accessioned | 2012-06-28T07:31:42Z | - |
dc.date.available | 2012-06-28T07:31:42Z | - |
dc.date.issued | 2011-05-07 | - |
dc.identifier.issn | 1477-0520 | - |
dc.identifier.uri | http://hdl.handle.net/2433/156967 | - |
dc.description.abstract | Amidine-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. | en |
dc.format.mimetype | application/pdf | - |
dc.language.iso | eng | - |
dc.publisher | Royal Society of Chemistry | en |
dc.rights | © The Royal Society of Chemistry 2011 | en |
dc.rights | 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.rights | This is not the published version. Please cite only the published version. | en |
dc.subject.mesh | Amidines/chemistry | en |
dc.subject.mesh | Amino Acids/chemistry | en |
dc.subject.mesh | Drug Design | en |
dc.subject.mesh | Esters/chemistry | en |
dc.subject.mesh | Ions/chemistry | en |
dc.subject.mesh | Molecular Structure | en |
dc.subject.mesh | Nitriles/chemistry | en |
dc.subject.mesh | Oxides/chemistry | en |
dc.subject.mesh | Peptides/chemical synthesis | en |
dc.subject.mesh | Peptidomimetics/chemical synthesis | en |
dc.title | Design and synthesis of amidine-type peptide bond isosteres: application of nitrile oxide derivatives as active ester equivalents in peptide and peptidomimetics synthesis. | en |
dc.type | journal article | - |
dc.type.niitype | Journal Article | - |
dc.identifier.ncid | AA1168650X | - |
dc.identifier.jtitle | Organic & biomolecular chemistry | en |
dc.identifier.volume | 9 | - |
dc.identifier.issue | 9 | - |
dc.identifier.spage | 3421 | - |
dc.identifier.epage | 3427 | - |
dc.relation.doi | 10.1039/c0ob01193b | - |
dc.textversion | author | - |
dc.identifier.pmid | 21423919 | - |
dcterms.accessRights | open access | - |
出現コレクション: | 学術雑誌掲載論文等 |
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