TAILIEUCHUNG - Báo cáo khoa học: A novel type of highly negatively charged lipooligosaccharide from Pseudomonas stutzeri OX1 possessing two 4,6-O-(1-carboxy)-ethylidene residues in the outer core region

Pseudomonas stutzeriOXI is a Gram-negative microorgan-ism able to grow in media containing aromatic hydrocar-bons. A novel lipo-oligosaccharide fromP. stutzeriOX1 was isolated and characterized. For the first time, the pres-ence of two moieties of 4,6-O-(1-carboxy)-ethylidene resi-dues (pyruvic acid) was identified in a core region; these two residues were found to possess different absolute configur-ation. The structure of the oligosaccharide backbone was determined using either alkaline or acid hydrolysis. . | Eur. J. Biochem. 271 2691-2704 2004 FEBS 2004 doi A novel type of highly negatively charged lipooligosaccharide from Pseudomonas stutzeri OX1 possessing two 4 6-ỡ- 1-carboxy -ethylidene residues in the outer core region Serena Leone1 Viviana Izzo2 Alba Silino1 Luisa Sturiale3 Domenico Garozzo3 Rosa Lanzetta1 Michelangelo Parrilli1 Antonio Molinaro1 and Alberto Di Donato2 1 Dipartimento di Chimica Organica e Biochimica and 2Dipartimento di Chimica Biologica Universita degli Studi di Napoli Federico II Napoli Italy 3Istituto per la Chimica e la Tecnologia dei Materiali Polimerici - ICTMP - CNR Catania Italy Pseudomonas stutzeri OXI is a Gram-negative microorganism able to grow in media containing aromatic hydrocarbons. A novel lipo-oligosaccharide from P. stutzeri OX1 was isolated and characterized. For the first time the presence of two moieties of 4 6-O- 1-carboxy -ethylidene residues pyruvic acid was identified in a core region these two residues were found to possess different absolute configuration. The structure of the oligosaccharide backbone was determined using either alkaline or acid hydrolysis. Alkaline treatment aimed at recovering the complete carbohydrate backbone was carried out by mild hydrazinolysis de-O-acylation followed by de-N-acylation using hot KOH. The lipo-oligosaccharide was also analyzed after acid treatment attained by mild hydrolysis with acetic acid to obtain information on the nature of the phosphate and acyl groups. The two resulting oligosaccharides were isolated by gel permeation chromatography and investigated by compositional and methylation analyses by MALDI mass spectrometry and by 1H- 31P- and 13C-NMR spectroscopy. These experiments led to the identification of the major oligosaccharide structure representative of core region-lipid A. All sugars are D-pyranoses and a-linked if not stated otherwise. Based on the structure found the hypothesis can be advanced that pyruvate residues are used to .

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