Solid-Phase Synthesis of Oxetane Modified Peptides
Beadle, J.D.; Knuhtsen, A.; Hoose, A.; Raubo, P.; Jamieson, A.G.; Shipman, M.
Organic Letters 19(12): 3303-3306
ISSN/ISBN: 1523-7052 PMID: 28585839 DOI: 10.1021/acs.orglett.7b01466
Solid-phase peptide synthesis (SPPS) is used to create peptidomimetics in which one of the backbone amide C═O bonds is replaced by a four-membered oxetane ring. The oxetane containing dipeptide building blocks are made in three steps in solution, then integrated into peptide chains by conventional Fmoc SPPS. This methodology is used to make a range of peptides in high purity including backbone modified derivatives of the nonapeptide bradykinin and Met- and Leu-enkephalin.