TER-117
Chemical Name: L-Glutamyl-S-(benzyl)-L-cysteinyl-D-phenylglycine
CAS No. 152684-53-2
项目整合开发状态: Preclinical
项目研究机构: Telik (Originator)
合成路线:D-Phenylglycine (I) was converted to ethyl ester (II) by means of ethanol and thionyl chloride.Coupling of N-Fmoc-S-benzylcysteine (III) with amino ester (II) produced the protected dipeptide (IV).The Fmoc group of (IV) was then removed by treatment with piperidine in DMF to give (V).N-Fmoc-glutamic acid alpha-benzyl ester (VII) was prepared by reaction of glutamic acid alpha-benzyl ester (VI) with N-(fluorenylmethoxycarbonyloxy)succinimide.Coupling of protected glutamic acid (VII) with dipeptide (V) furnished tripeptide (VIII).The Fmoc and ester protecting groups of (VIII) were finally cleaved by treatment with NaOH.
📌 参考资料/链接：
参考文献标题:Glutathione analogs and paralog panels comprising glutathione mimics
文献作者:Kauvar,L.M.; Lyttle,M.H.(Telik,Inc.)
参考来源:EP 0720620; US 5599903; WO 9508563
📄 详细内容
合成路线:D-Phenylglycine (I) was converted to ethyl ester (II) by means of ethanol and thionyl chloride.Coupling of N-Fmoc-S-benzylcysteine (III) with amino ester (II) produced the protected dipeptide (IV).The Fmoc group of (IV) was then removed by treatment with piperidine in DMF to give (V).N-Fmoc-glutamic acid alpha-benzyl ester (VII) was prepared by reaction of glutamic acid alpha-benzyl ester (VI) with N-(fluorenylmethoxycarbonyloxy)succinimide.Coupling of protected glutamic acid (VII) with dipeptide (V) furnished tripeptide (VIII).The Fmoc and ester protecting groups of (VIII) were finally cleaved by treatment with NaOH.
参考文献标题:Isozyme-specific glutathione-S-transferase: Design and synthesis
文献作者:Lyttle,M.H.; Hocker,M.D.; Hui,H.C.; Caldwell,C.G.; Aaron,D.T.; Engqvist-Goldstein,A.; Flatgaard,J.E.; Bauer,K.E.
参考来源:J Med Chem 1994,37(1),189
产品链接: CAS No. 152684-53-2››