Development of solid-supported methodology for the preparation of peptidoglycan fragments containing (2S,6R)-diaminopimelic acid

Abstract Herein, we describe the development of an efficient solid-supported methodology for the stereoselective synthesis of two peptides containing (2 S ,6 R )-diaminopimelic acid, ( S )-Ala-γ-( R )-Glu-(2 S ,6 R )-A 2 pm-( R )-Ala 1 and γ-( R )-Glu-(2 S ,6 R )-A 2 pm 2 . The platform consists of a Wang resin anchored by an amino acid chain including allylglycine. By olefin cross metathesis with vinylglycine, unsaturated protected (2 S ,6 R )-A 2 pm was fixed on solid support. Peptides were achieved by cleavage of cross metathesis products from resin, followed by reduction of double bonds along removing of protecting groups. Furthermore, this efficient solid phase approach will lead to peptide and muropeptide libraries.