The synthesis of cyclic peptides by chemoselective cyclization reactions was studied. A resin-bound amino acid was reductively alkylated using an appropriate aldehyde and the resulting secondary amine was then acylated to yield an N-alkylated dipeptide. Deprotection was followed by cleavage using toluene-ethanol solvent mixtures under acidic or basic conditions induced cyclization to yield Diketopiperazines (DKPs). It was concluded that the diverse functionality presented by unprotected linear peptides presented a unique challenge to selective intramolecular connections between different points of the peptide chain.
|Number of pages||14|
|Journal||Journal of the Chemical Society. Perkin Transactions 1|
|Publication status||Published - 7 Mar 2001|