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Formation of N-(1-ferrocenoylpyrrolidine-2-carbonyl)-N,N′-dicyclohexylurea: Dead-end in the preparation of ferrocene-modified peptides
Authors:Anas Lataifeh
Institution:Department of Chemistry, University of Western Ontario, 1151 Richmond Street, London, Ontario, Canada N6A 5B7
Abstract:This paper reports the synthesis, characterisation and electrochemical properties of Fc-Pro-DCU 3. The activation of Fc-Pro-OH with DCC in the absence of racemization reducing agent results in the formation of N-(1-ferrocenoylpyrrolidine-2-carbonyl)-N,N′-dicyclohexylurea, as result of O/N-acyl shift in the acylisourea intermediate. Compound 3 exhibits quasi-reversible one-electron oxidation of ferrocenoyl moiety at E1/2 = 0.62 V.
Keywords:Carbodiimides  N-Acylurea  Ferrocene  Electrochemistry  Bioorganometallic chemistry
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