Toman R, Skultety L, Ftacek P, Hricovini M NMR study of virenose and dihydroxystreptose isolated from Coxiella burnetii phase I lipopolysaccharide Carbohydrate Research306 (1998)
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NCBI PubMed ID:9691453 Journal NLM ID:0043535 Publisher: Elsevier Correspondence: virutomasavba.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.
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
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