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pubmed-article:18613286pubmed:issue11lld:pubmed
pubmed-article:18613286pubmed:dateCreated2008-10-27lld:pubmed
pubmed-article:18613286pubmed:abstractTextA novel strategy for a more efficient synthesis of difficult sequence-containing peptides, the S-acyl isopeptide method, was developed and successfully applied. A model pentapeptide Ac-Val-Val-Cys-Val-Val-NH2 was synthesized via its water-soluble S-acyl isopeptide using an S-acyl isodipeptide unit, Boc-Cys(Fmoc-Val)-OH. An S-acyl isopeptide possessing excellent water solubility could be readily and quantitatively converted to the native peptide via an S--N intramolecular acyl migration reaction at pH 7.4. Thus, the S-acyl isopeptide method provides a useful tool in peptide chemistry.lld:pubmed
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pubmed-article:18613286pubmed:authorpubmed-author:KuoS PSPlld:pubmed
pubmed-article:18613286pubmed:authorpubmed-author:KimuraTooruTlld:pubmed
pubmed-article:18613286pubmed:authorpubmed-author:KisoYoshiakiYlld:pubmed
pubmed-article:18613286pubmed:authorpubmed-author:YoshiyaTakuTlld:pubmed
pubmed-article:18613286pubmed:copyrightInfoCopyright (c) 2008 European Peptide Society and John Wiley & Sons, Ltd.lld:pubmed
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pubmed-article:18613286pubmed:volume14lld:pubmed
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pubmed-article:18613286pubmed:year2008lld:pubmed
pubmed-article:18613286pubmed:articleTitleIsopeptide method: development of S-acyl isopeptide method for the synthesis of difficult sequence-containing peptides.lld:pubmed
pubmed-article:18613286pubmed:affiliationDepartment of Medicinal Chemistry, Division of Medicinal Chemical Sciences, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina-ku, Kyoto, Japan.lld:pubmed
pubmed-article:18613286pubmed:publicationTypeJournal Articlelld:pubmed
pubmed-article:18613286pubmed:publicationTypeResearch Support, Non-U.S. Gov'tlld:pubmed