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J. Biol. Chem., Vol. 277, Issue 12, 10058-10063, March 22, 2002

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Lipopolysaccharides Possessing Two L-Glycero-D-manno-heptopyranosyl--(15)-3-deoxy-D-manno-oct-2-ulopyranosonic Acid Moieties in the Core Region
THE STRUCTURE OF THE CORE REGION OF THE LIPOPOLYSACCHARIDES FROM BURKHOLDERIA CARYOPHYLLI^*

Antonio Molinaro^§, Cristina De Castro, Rosa Lanzetta, Antonio Evidente^¶, Michelangelo Parrilli, and Otto Holst^§

From the  Dipartimento di Chimica Organica e Biochimica, Università degli studi di Napoli "Federico 11," I-80126 Napoli, Italy, the ^§ Division of Structural Biochemistry, Research Center Borstel, Center for Medicine and Biosciences, D-23845 Borstel, Germany, and the ^¶ Dipartimento di Scienze Chimico-Agrarie, Università degli studi di Napoli "Federico 11," I-80055 Portici, Italy

The carbohydrate backbone of the core-lipid A region was characterized from the lipopolysaccharides (LPSs) of the plant-pathogenic bacterium Burkholderia caryophylli. For the first time, the presence of two moieties of L-glycero-D-manno-heptopyranosyl--(15)-3-deoxy-D-manno-oct-2-ulopyranosonic acid was identified in a core region, which is of particular interest with regard to the biosynthesis of this and of LPSs in general. The LPSs of B. caryophylli were degraded by mild hydrazinolysis (de-O-acylation), treatment with 48% aqueous HF at 4 °C (cleavage of phosphate groups and destruction of the O-specific polysaccharides), reduction with NaBH4, and de-N-acylation utilizing hot KOH. The major oligosaccharide representing the carbohydrate backbone of the core region and lipid A was isolated by high-performance anion-exchange chromatography. Its analysis employing compositional and methylation analyses, matrix-assisted laser desorption/ionization mass spectrometry, and ¹H and ¹³C NMR spectroscopy applying various one-dimensional and two-dimensional experiments identified the following structure.

All sugars are pyranoses and -linked, if not stated otherwise. Hep is L-glycero-D-manno-heptose, Kdo is 3-deoxy-D-manno-oct-2-ulosonic acid.

This article is dedicated to Professor Lorenzo Mangoni on the occasion of his 70th birthday.

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