新产品编号:214079
Chemical Name: N-(N-Phenylcarbamoyl)-L-seryl-L-leucyl-L-valine ethyl ester
CAS No. 189110-11-0
项目整合开发状态: Biological Testing
项目研究机构: Kirin Brewery (Originator)
合成路线:The title compound was obtained by the solid-phase method using a peptide synthesizer.Starting from Fmoc-valine linked to Wang resin (I),cleavage of the Fmoc group with piperidine in DMF provided the deprotected valine-resin (II),which was then coupled with Fmoc-leucine (III) by means of 1-hydroxybenzotriazole and diisopropylcarbodiimide.The resulting dipeptide resin (IV) was deprotected with piperidine in DMF to give (V),and further coupling with protected serine (VI) yielded (VII).After Fmoc-deprotection,the tripeptide-resin (VIII) was coupled with phenyl isocyanate (IX),affording urea (X).Cleavage from the resin with simultaneous deprotection using trifluoroacetic acid furnished the tripeptide urea (XI).This was finally esterified by treatment with ethanolic HCl to provide the target ethyl ester.
📌 参考资料/链接：
参考文献标题:Novel peptide cpds.and medicinal compsns.thereof
文献作者:Kataoka,S.; Nishitoba,T.; Takahashi,M.; Sawa,E.; Kamishohara,M.(Kirin Brewery Co.,Ltd.)
参考来源:JP 1999171896; WO 9711091
📄 详细内容
合成路线:The title compound was obtained by the solid-phase method using a peptide synthesizer.Starting from Fmoc-valine linked to Wang resin (I),cleavage of the Fmoc group with piperidine in DMF provided the deprotected valine-resin (II),which was then coupled with Fmoc-leucine (III) by means of 1-hydroxybenzotriazole and diisopropylcarbodiimide.The resulting dipeptide resin (IV) was deprotected with piperidine in DMF to give (V),and further coupling with protected serine (VI) yielded (VII).After Fmoc-deprotection,the tripeptide-resin (VIII) was coupled with phenyl isocyanate (IX),affording urea (X).Cleavage from the resin with simultaneous deprotection using trifluoroacetic acid furnished the tripeptide urea (XI).This was finally esterified by treatment with ethanolic HCl to provide the target ethyl ester.
参考文献标题:Structural modification of Fas C-terminal tripeptide and its effects on the inhibitory activity of Fas/FAP-1 binding
文献作者:Sawa,E.; Takahashi,M.; Kamishohara,M.; Tazunoki,T.; Kimura,K.; Arai,M.; Miyazaki,T.; Kataoka,S.; Nishitoba,T.
参考来源:J Med Chem 1999,42(17),3289