A lipopolysaccharide (LPS) isolated from Coxiella burnetiii in virulent phase I contains in its O-polysaccharide chain two unusual sugars, virenose (6-deoxy-3-C-methylgulose) and dihydrohydroxystreptose [3-C-(hydroxymethyl)lyxose]. The sugars were isolated from LPS I, after acid hydrolysis and removal of lipid A, by a combination of HPLC and preparative paper chromatography. Their enantiomeric forms and ring conformations were established from optical rotation and NMR data. Two-dimensional COSY, HSQC, and HMBC as well as one- and two-dimensional NOEs were used to assign all proton and carbon signals in both monosaccharides. Virenose was found to be the D-gulo enantiomer with the 4C1 ring conformation and dihydrohydroxystreptose was shown to be the L-lyxo enantiomer also with the 4C1 conformation. The latter sugar was reported [S. Schramek, J. Radziejewska-Lebrecht, and H. Mayer, Eur. J. Biochem., 148 (1985) 455-461] to be present in LPS I in a furanose form, and it appears that a furanose to pyranose tautomerization took place in the course of the isolation procedure.
Lipopolysaccharide, Coxiella burnetii, Virenose, Dihydrohydroxystreptose, NMR ring conformations, Tautomerization
NCBI PubMed ID: 9691453Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: virutoma@savba.savba.sk
Institutions: Institute of Virology, Slovak Academy of Sciences, Dubravska cesta 9, Bratislava 842 46, Slovak Republic, Institute of Chemistry, Slovak Academy of Sciences, Dubravska cesta 9, Bratislava 842 38, Slovak Republic.
Methods: NMR-2D, NMR, paper chromatography
Found