Solid phase synthesis of cyclic peptides: model studies involving i-(i+4) side chain-to-side chain cyclisation.
Conditions for the synthesis of i-(i + 4) side chain-to-side chain head-to-tail Lys-->Glu and Glu-->Lys linked cyclic peptides related to hypoglycaemic analogues of human growth hormone hGH [6-13] have been examined. The success of the cyclisation reaction with the corresponding resin-bound, partially protected linear peptides was found to be both reagent as well as sequence dependent, with competing inter-chain oligomerisation predominating in some cases. The results also indicated that protection with the bulky Fmoc group of the amino acid residues immediately adjacent to the side chain-deprotected Lys and Glu residues, which participate in the cyclisation reaction, enhanced the rate of lactam formation.
Cavallaro
V
V
Centre for Bioprocess Technology, Department of Biochemistry and Molecular Biology, Monash University, Clayton, Australia.
Thompson
P
P
Hearn
M
M
D006801:Humans; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry*
D010456:Peptides, Cyclic