Linear synthesis and conformational analysis of the pentasaccharide repeating unit of the cell wall O-antigen of Escherichia coli O13

Carbohydr Res. 2014 Jun 4:391:9-15. doi: 10.1016/j.carres.2014.03.012. Epub 2014 Mar 20.

Abstract

Synthesis of the pentasaccharide repeating unit of the O-antigen of Escherichia coli O13 strain has been achieved using a straightforward linear synthetic strategy. Similar reaction conditions have been used for all glycosylations as well as protective group manipulations. All intermediate steps are high yielding and the glycosylation steps are stereoselective. The synthesized pentasaccharide was subjected to conformational analysis using 2D ROESY NMR spectral analysis and molecular dynamics (MD) simulation to get detailed information on conformation of the molecule in aqueous solution.

Keywords: Conformational analysis; Escherichia coli; Molecular dynamics simulation; O-Antigen; Pentasaccharide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Cell Wall / chemistry*
  • Escherichia coli / chemistry*
  • Escherichia coli / cytology*
  • O Antigens / chemistry*
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry

Substances

  • O Antigens
  • Oligosaccharides