Synthetic approaches to versatile hemoprotein model compounds built from porphyrins and peptides

Abstract

Several strategies for the preparation of mono- and bi-functional porphyrins (amino and carboxylate) to which oligopeptides can be attached have been investigated. A porphyrinyl amino-acid derivative has been synthesised by coupling a porphyrin monopropionate with phenylalanine methyl ester. Routes to pyrroles bearing butoxycarbonylaminoethyl side-chains via Curtius-type degradations, are described, and their potential for elaboration into porphyrins is discussed. The most promising bifunctional porphyrin with differentially protected amino and carboxylate side-chains was found to be the butoxycarbonylhydrazido methyl ester derivative of mesoporphyrin-II.