Solid-phase synthesis of peptides containing bulky dehydroamino acids

Abstract A method of incorporating bulky α,β-dehydroamino acids such as dehydrovaline and dehydroethylnorvaline into peptides via solid-phase peptide synthesis is reported. The key step involves ring opening of an azlactone (i.e., oxazolone) containing the dehydroamino acid by the amino group of a resin-bound peptide. The use of Alloc-protected azlactones was key to the success of the process.