The unique structure of complete lipopolysaccharide isolated from semi-rough Plesiomonas shigelloides O37 (strain CNCTC 39/89) containing (2S)-O-(4-oxopentanoic acid)-α-D-Glcp (α-D-Lenose)

Abstract

The complete structure of semi-rough lipopolysaccharide (SR-LPS) of Plesiomonas shigelloides CNCTC 39/89 (serotype O37) has been investigated by (1)H and (13)C NMR spectroscopy, matrix-assisted laser-desorption/ionization time-of-flight MS, and chemical methods. The following structure of the single unit of the O-antigen has been established: [formula see text] in which α-D-Lenp is (2S)-O-(4-oxopentanoic acid)-α-D-Glcp residue which has not been found in nature. The absolute configuration of oxopentanoic acid moiety in α-d-Lenose residue was determined by NOESY experiment combined with molecular modeling (MM2 force field). The decasaccharide core is substituted at C-4 of the β-D-Glcp residue with a single pentasaccharide unit. Lipid A is built of a β-D-GlcpN4P-(1→6)-α-D-GlcpN1P disaccharide asymmetrically substituted with fatty acids. It was concluded that the core oligosaccharide and the lipid A are identical with those in P. shigelloides CNCTC 113/92 Niedziela et al. (2002)(9) and Lukasiewicz et al. (2006).(10.)

Keywords: CNCTC; COSY; Czech National Collection of Type Cultures; DEPT; GC; HMBC; HSQC; MALDI-TOF; MALDI-TOF MS; MM2; MM2 force field; MS; NMR; NOESY; OS; Oxopentanoic acid; Plesiomonas shigelloides; SR-LPS; Semi-rough lipopolysaccharide; TOCSY; correlated spectroscopy; distortionless enhancement by polarization transfer; gas chromatography; heteronuclear multiple bond correlation; heteronuclear single quantum coherence; mass spectrometry; matrix-assisted laser-desorption/ionization time-of-flight; molecular mechanics version; nuclear Overhauser effect spectroscopy; nuclear magnetic resonance; oligosaccharide; semi-rough lipopolysaccharide; total correlation spectroscopy.