SYNTHESIS OF A CYCLIC ANALOG OF THE C-LOOP REGION OF EPIDERMAL GROWTH-FACTOR, CONTAINING 1-AMINOCYCLOPROPANE-1-CARBOXYLIC ACID

We report the synthesis of a cyclic analogue of epidermal growth facto r sequence 33-42 with substitution of 1-aminocyclopropane-1-carboxylic acid for glycine at position 39 tyl-Cys-Val-Ile-Gly-Tyr-Ser-ACPCAAsp- Arg-Cys-NH2). The analogue was synthesised by solid-phase methods, usi ng t-Boc chemistry and acid-labile side-chain protecting groups. The u se of the 4-methoxybenzyl protecting group for C- and N-terminal cyste ine residues resulted in the spontaneous formation of the desired intr amolecular disulfide bond after HF deprotection. (C) Munksgaard 1994.