Analogs of the cytostatic cyclic tetrapeptide chlamydocin. Synthesis of N. beta.-(N-maleoylglycyl) and N. beta.-(tert-butyloxycarbonyl) derivatives of cyclo (Gly-L-Phe-D- …

DH Rich, RD Jasensky, GC Mueller…

Index: Rich; Jasensky; Mueller; Anderson Journal of Medicinal Chemistry, 1981 , vol. 24, # 5 p. 567 - 572

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Citation Number: 20

Abstract

The synthesis of analogues of the cytostatic cyclic tetrapeptide chlamydocin is described. cyclo (G1y-L-Phe-D-Pro-NP-Boc-L-Dap)(4) was prepared from I@-(tert-butyloxycarbony1)-L- diaminopropionic acid methyl ester (Dap) and Cbz-Gly-L-Phe-D-Pro using DCC/HOBt as the coupling reagent. The methyl ester was saponified to the acid, which was converted to the 2, 4, 5-trichlorophenyl (Tcp) ester by reaction with trichlorophenol and DCC. The N-( ...