A powerful synthetic method, cyclo-oligomerization allows efficient formation of various macrocyclic peptides, with the potential to create a plethora of dimer, trimer, and tetramer macrocycles for applications in medicine, drug design, and catalysis. Formation of diketopiperazines from intramolecular cyclization of dipeptide segments of natural amino acids occurs under N-deprotection and carboxyl group activation. Peptide segments containing �-turn inducing constraint element increases the difficulty of intra-molecular cyclizations; such segments include: oxazolines, oxazoles, thiazolines, thiazoles and imidazoles. Their rigid transconformations and five-membered ring structures therefore make them ideal to serve as building blocks for the proposed synthetic strategies.In our previous investigations, we showed that the synthesis of cyclo-tetrapeptides can be achieved utilizing a palladium catalyzed tandem deprotection/macrocyclization strategy with readily available cbz-dipeptidoyl benzotriazolides. We now report that cbz-dipeptidoyl benzotriazolides can be cyclized intra-molecularly or in a cyclo-oligomerization fashion to access different peptide macrocycles.

Intra-molecular lactamization and cyclo-oligomerization of dipeptidoyl benzotriazolides in synthesis of cyclo-peptides

247th National Meeting (2014)

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