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

作者：Simon Justine F^*; Lamborelle Nicolas; Zervosen Astrid; Lemaire Christian; Joris Bernard; Luxen Andre

来源：Tetrahedron Letters, 2016, 57(14): 1572-1575.

DOI：10.1016/j.tetlet.2016.02.098

• (2S,6R)-Diaminopimelic acid
• Peptide and muropeptide libraries
• Solid phase platform
• Heterogeneous olefin cross metathesis

Herein, we describe the development of an efficient solid-supported methodology for the stereoselective synthesis of two peptides containing (2S,6R)-diaminopimelic acid, (S)-Ala-gamma-(R)-Glu-(2S,6R)-A(2)pm-(R)-Ala 1 and gamma-(R)-Glu-(2S,6R)-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 (2S,6R)-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.

• 出版日期2016-4-6