Synthesis of Peptidoglycan Fragments from Enterococcus faecalis with Fmoc-Strategy for Glycan Elongation

Abstract

Peptidoglycan (PGN) is an essential structural component of the bacterial cell wall conferring cell shape, which can be recognized by host-recognition proteins and receptors as well as bacterial surface proteins. In this work, the PGN partial structures from Enterococcus faecalis that contain a tetrasaccharide and an octasaccharide with a unique heptapeptide were synthesized via an Fmoc-strategy for elongation of the glycan chains. Namely, a 4'-O-Fmoc-protected disaccharide was utilized as the key intermediate in this efficient synthetic pathway for preparing various PGN fragments. Both the tetrasaccharide and octasaccharide with the unique heptapeptide were successfully synthesized for the first time.

Keywords: bioorganic chemistry; carbohydrates; glycosylation; peptides; peptidoglycan.