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Journal of Endotoxin Research
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Synthesis and purification by HPLC of des-O-acyl partial structures of Escherichia coli Re lipopolysaccharide

K. Fukase

Department of Chemistry, Faculty of Science, Osaka University, Osaka, Japan

M. Kurosawa

Department of Chemistry, Faculty of Science, Osaka University, Osaka, Japan

S. Kusumoto

Department of Chemistry, Faculty of Science, Osaka University, Osaka, Japan

Four compounds corresponding to partial structures of Re-type lipopolysaccharide (LPS) were synthesized for precise investigation of immunological properties of the 3-deoxy-D-manno-2-octulosonic acid (Kdo)-containing inner core and lipid A regions of LPS. The synthetic compounds lack all the ester-bound acyl groups which are present in natural LPS but known to be not essential for the antigenicity. The simplest compound is N,N'-diacylated glucosamine β1-6 disaccharide 4'-monophosphate 2 which corresponds to the des-O-acyl derivative of 1-dephospho lipid A. The other three contain one or two Kdo moieties linked to 2. The most complex one is a tetrasaccharide equivalent to the des-O-acylated 1-dephosphorylated derivative of LPS from Escherichia coli Re-mutant. Syntheses were performed by stepwise condensation of appropriately protected sugar moieties and final hydrogenolytic deprotection. The synthetic des-O-acyl LPS analogs were effectively purified by means of reversed phase HPLC to give homogeneous preparations.

Journal of Endotoxin Research, Vol. 1, No. 3, 149-163 (1994)
DOI: 10.1177/096805199400100304
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