The core oligosaccharide component from Mannheimia (Pasteurella) haemolytica serotype A1 lipopolysaccharide contains L- glycero -D- manno - and D- glycero -D- manno -heptoses. Analysis of the structure and conformation by high resolution NMR spectroscopy

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TypeArticle
Journal titleCanadian Journal of Chemistry
Volume80
Issue8
Pages949963; # of pages: 15
Subject13C; 13C-NMR; 1D; 1H; 2D; 31P; analysis; chemical; chemical shift; CHEMICAL-SHIFTS; COMPONENT; COMPONENTS; conformation; CONFORMATIONAL; conformational analysis; CONFORMATIONAL-ANALYSIS; core oligosaccharide; COUPLING; coupling constants; COUPLING-CONSTANTS; Form; FORMS; HETEROGENEITY; HETERONUCLEAR; HIGH-RESOLUTION; Laboratories; LINKAGES; lipid; Lipid A; LIPID-A; LIPOPOLYSACCHARIDE; LPS; method; Methods; MODEL; MOLECULAR; MONOSACCHARIDES; MONTE CARLO; Monte Carlo Method; NMR; NMR spectroscopy; NMR-spectroscopy; oligosaccharide; PROTON; REGION; RESIDUES; RESOLUTION; Resolution Nmr Spectroscopy; SACCHARIDES; selective; SEROTYPE; shifts; SPECTROSCOPY; STRUCTURAL; structure
AbstractPrevious studies from our laboratory have indicated that the lipopolysaccharide (LPS) from Mannheimia haemolytica serotype A1 contains both L- glycero -D- manno -heptose and D- glycero -D- manno -heptose residues. NMR methods making use of 1D 1H selective excitation and 2D (1H, 13C) and (1H, 31P) heteronuclear experiments were used for the structural determination of the major core oligosaccharide components of the deacylated low-molecular-mass LPS obtained following sequential treatment with anhydrous hydrazine and aq KOH. The core oligosaccharide region was found to be composed of a branched octasaccharide linked to the deacylated lipid A moiety via a 3-deoxy-4-phospho-D- manno -oct-2-ulosonate residue having the structure (see text). Heterogeneity was found to be present at several linkages. NMR methods were devised to distinguish between the diastereomeric forms of the heptose residues. Synthesized monosaccharides of L-D- and D-D-heptose were used as model compounds for analysis of the 1H and 13C NMR chemical shifts and proton coupling constants. Molecular modeling using a Monte Carlo method for conformational analysis of saccharides was used to determine the conformation of the inner core of the oligosaccharide and to establish the stereochemical relationships between the heptoses.
Publication date
LanguageEnglish
AffiliationNRC Institute for Biological Sciences; National Research Council Canada
Peer reviewedNo
NRC numberBRISSON2002A
NPARC number9362440
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Record identifier8484dd60-c00f-45e6-a2cc-cad5d74b2d4b
Record created2009-07-10
Record modified2016-05-09
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