Specific polysaccharides of the lipopolysaccharides of Gram-negative bacteria

This review generalizes the result of structural investigations of the polysaccharides of the O-specific side chains of the lipopolysaccharides (LPSs) of the most studied representations of the family Enterobacteriaceae. The O-specific polysaccharides are the serologically dominating part of the molecule that is responsible for the O-antigenic specificity of the LPSs. The structures of the specific polysacchrides from various Gram-positive bacteria are given. The serological specificity of the O-antigens is discussed and a connection is shown between the chemical structures of the polysaccharides and their serological affinity.     

Lipopolysaccharides of the pseudotuberculosis microbe Yersinia pseudotuberculosis

This review generalizes the results of structural investigations of the polysaccharides of the O-specific side chains, of the core oligosaccharides, and of the lipid A of the pseudotuberculosis microbeYersinia pseudotuberculosis which causes Far-Eastern scarlatina-like fever. The complete structures of the repeating units of the specific polysaccharides from the lipopolysaccharides of serovars I A, I B, III, IV A, V A, V B, and VI which are responsible for the O-antigenic specificity of the microorganism are given. For the majority of serovars the repeating unit is represented by a branched pentasaccharide. Exceptions are the lipopolysaccharides of serovars I A and III which have a tetrasaccharide repeating unit. The presence of an aminosugar residue at the reducing end, by which the O-specific chain is attached to the oligosaccharide of the core, is common and characteristic for the lipopolysaccharides isolated from all the serovars. The structures of the core oligosaccharide and of lipid A, which are common for all serovars ofYersinia pseudotuberculosis, are given.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, USSR Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 163–171, March–April, 1988.     

Chemical and immunochemical investigation of the lipopolysaccharides ofVibrio alginolyticus

A chemical and immunochemical study of the LPSs of the microorganismsVibrio alginolyticus (strains 1385–80, 945–80, and 2076–80) has been made. A difference in the monosaccharide composition of the LPSs of the strains studied has been shown. It had been established that the LPSs of strains 945–80 and 2076–80 possess a high serological specificity, while the LPS of strain 1385–80 differ serologically from them. A suggestion is made of the role of different monosaccharides in the formation of the immunochemical determinants of the LPSs of the strains studied.Pacific Ocean Institute of Bioorganic Chemistry of the Far-Eastern Scientific Center of the USSR Academy of Sciences, Vladivostok. Translated from Khimiya Priorodnykh Soedinenii, No. 5, pp. 652–657, September–October, 1987.     

Unusual monosaccharides in the O-factors of lipopolysaccharides of Gram-negative bacteria

Information is generalized on the structure of the O-specific polysaccharides forming components of the lipopolysaccharides of Gram-negative bacteria in which residues of unusual monosacchrides rarely found in nature have been identified. A chemical substantiation of the immunological specificity of the O-factors of specific chains is given. The role of the unusual monosaccharides in the manifestation of O-factor specificity is discussed.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, USSR Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 743–763, November–December, 1989.     

Structure and serology of O-antigens of nitrogen-fixing rhizobacteria of the genus <Emphasis Type="Italic">Azospirillum</Emphasis>

The review presents a discussion of the published data of 2002 to 2014 dealing with structural studies of O-specific polysaccharides, representatives of the Azospirillum diazotrophic rhizobacteria, summarizing the results of a series of authors´ studies. Some general structures incorporated in O-specific polysaccharides responsible for classification of bacterial cultures into serogroups on the basis of immunochemical studies were characterized. The structures of O-specific polysaccharides of seven azospirillum strains identical to those of previously studied strains are presented in this review for the first time.     

Comparative structural study of the lipopolysaccharides of Y. enterocolitica serovars 0:7.8 and 0:19.8

The lipopolysaccharides ofYersinia enterocolitica, serovars 0:7.8 (strain 106) and 0:19.8 (strain 842), isolated from the microbial mass by phenol-water extraction, contained residues of L-fucose, 6-deoxy-D-gulose, D-mannose, D-galactose, D-glucose, D- and L-glycero-D-mannoheptoses, N-acetyl-D-glucosamine, N-acetyl-D-galactosamine, and 2-keto-3-deoxyoctonic acid (KDO). The polysaccharides obtained by mild acid hydrolysis of the lipopolysaccharides followed by gel filtration on Sephadex G-50 were a mixture of the O-specific polysaccharide and the core, which could not be separated even by repeated rechromatography because of the comparability of their molecular masses. On the basis of the results of monosaccharide analysis, methylation, Smith degradation, and partial hydrolysis, a structure has been suggested for the repeating unit of the O-specific polysaccharides of the lipopolysaccharides ofY. enterocolitica of the serovars studied.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, USSR Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 763–770, November–December, 1989.     

Synthesis of the principal chain of the o-antigenic polysaccharides ofShigella flexneri. Communication 6. Synthesis of the monomer,its polycondensation,and properties of the polysaccharide

Conclusions Regio- and stereospecific polycondensation has been used to synthesize the principal chain of the O-specific polysaccharides of the bacteriumSh. flexneri. Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1151–1156, May, 1985.For Communication 5, see [1].     

Chemical and immunochemical investigation of the lipopolysaccharides ofVibrio alginolyticus

A chemical and immunochemical study of the LPSs of the microorganismsVibrio alginolyticus (strains 1385–80, 945–80, and 2076–80) has been made. A difference in the monosaccharide composition of the LPSs of the strains studied has been shown. It had been established that the LPSs of strains 945–80 and 2076–80 possess a high serological specificity, while the LPS of strain 1385–80 differ serologically from them. A suggestion is made of the role of different monosaccharides in the formation of the immunochemical determinants of the LPSs of the strains studied.     

Lipids and lipopolysaccharides of the genusFlavobacterium

The fatty acid compositions of the free lipids of three strains and the monosaccharide compositions of the lipopolysaccharides of four strains of new species of microorganisms of the genusFlavobacterium have been studied. The acidic nature of the polysaccharides of the LPSs of the microorganisms studied has been shown.Pacific Ocean Institute of Bioorganic Chemistry of the Far Eastern Scientific Center of the USSR Academy of Sciences, Vladivostok, and Institute of Microbiology of the USSR Academy of Sciences, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 564–567, September–October, 1986.     

Synthesis of antigenic bacterial polysaccharides and their fragments

Conclusions The free trisaccharide-D-mannopyranosyl(1-4)--L-rhamnopyranosyl(1 3)-D-galactopyranose was obtained, which is the repeating unit of the backbone chain of the O-specific polysaccharides ofSalmonella of serological groups A, B, and D₁.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No.1, pp.165–167, January, 1976.     

Unusual monosaccharides in the O-factors of lipopolysaccharides of Gram-negative bacteria

Information is generalized on the structure of the O-specific polysaccharides forming components of the lipopolysaccharides of Gram-negative bacteria in which residues of unusual monosacchrides rarely found in nature have been identified. A chemical substantiation of the immunological specificity of the O-factors of specific chains is given. The role of the unusual monosaccharides in the manifestation of O-factor specificity is discussed.     

Lipopolysaccharides of marine blue-green algae

The lipopolysaccharides (LPSs) have been isolated from two blue-green algae,Oscillatoria hilderbrandtii andNostoc sp. by the method of phenol-water extraction. The LPSs contain polysaccharide and lipid components. The polysaccharide fraction fromO. hildebrandtii consists predominantly of 1,3-bound rhamnose residues with a substituent in the second position. The rhamnose residues in the polysaccharide fraction ofNostoc are connected by 1,3- and 1,2-glycosidic bonds. The lipid components of the LPSs fromO. hilderbrandtii andNostoc consist of palmitic and steric acids, with glucosamine and glucose.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 493–496, July–August, 1985.     

Polysaccharides of brown algae VIII. A study of pelvecyan and sargassan by methylation

Conclusions It has been shown by the methylation method that pelvecyan and sargassan are polysaccharides of similar structures with a high degree of branching of the carbohydrate chains. Fucose, xylose, and galactose are located at the nonreducing ends of their molecules, and mannose and galactose form points of branching of the carbohydrate chains of these polysaccharides.The positions of the bonds between the monosaccharide residues in pelvecyan and sargassan have been determined.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 142–145, March–April, 1974.     

Mass‐Spectrometric Studies of Providencia SR‐Form Lipopolysaccharides and Elucidation of the Biological Repeating Unit Structure of Providencia rustigianii O14‐Polysaccharide

Enterobacteria Providencia are opportunistic human pathogens causing multiple types of infections. Earlier we have studied the S‐ and R‐form lipopolysaccharides (LPSs) of Providencia strains of various O‐serogroups and established the structures of the O‐polysaccharides (O‐antigens) and core‐region oligosaccharides, respectively. Now we report on mass spectrometric studies of oligosaccharides consisting of the core moiety with one O‐polysaccharide repeating unit attached, which were derived from the SR‐form LPSs of Providencia strains. The site of attachment of the O‐polysaccharide to the core and the structure of the O‐polysaccharide biological repeating unit were elucidated in Providencia rustigianii O14 using NMR spectroscopy.     

Arabinoglucuronoxylans of the stems ofFagopyrum sagittatum andPolygonum wegrichii

The primary structures of the arabinoglucuronoxylans of the stems of common buckwheat andPolygonum weyrichii have been established. It has been shown that the polysaccharides differ by their degrees of branching and also by the nature of the addition of certain side chains.M. V. Lomonosov Odessa Technological Institute of the Food Industry. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 160–165, March–April, 1984.     

Kdo Glycosylations and Their Application in Oligosaccharide Synthesis**

Higher carbon saccharide 3-deoxy-d -manno-oct-2-ulosonic acid (Kdo) is a structural unit of bacterial lipopolysaccharides (LPSs) and capsular polysaccharides (CPSs). Kdo is present in the inner core region of LPSs, and this region is structurally conserved. Being non-mammalian in origin, Kdos are effectively recognized by the native and adaptive immune systems. Therefore, the synthesis of new Kdo derivatives and neoglycoconjugates is highly important for the development of vaccines. This review highlights recent accomplishments related to α-glycosylations, β-glycosylations and C-glycosylations of Kdos and their application to the stereoselective synthesis of inner core oligosaccharides.     

Galactans and galactan-containing polysaccharides of higher plants

Research on the chemical structure and physiological activity of galactan and galactan-containing polysaccharides of higher plants is reviewed. The principal chain in galactan-containing polysaccharides consists of 1–3, 1–4, 1–6, and - and -bonded D-galactopyranoses. The side chains contain separate or bonded chains of galactose, arabinose, glucose, rhamnose, and uronic acids. The relationship of chemical structure and physiological activity of the polysaccharides of higher plants is discussed.S. Yu. Yunusov Institute of the Chemistry of Plant Substances. Academy of Sciences of the Republic of Uzbekistan, Tashkent. fax (99871) 120 64 75. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 185–197, May–June, 2000.     

Comparative structural study of the lipopolysaccharides of Y. enterocolitica serovars 0:7.8 and 0:19.8

The lipopolysaccharides ofYersinia enterocolitica, serovars 0:7.8 (strain 106) and 0:19.8 (strain 842), isolated from the microbial mass by phenol-water extraction, contained residues of L-fucose, 6-deoxy-D-gulose, D-mannose, D-galactose, D-glucose, D- and L-glycero-D-mannoheptoses, N-acetyl-D-glucosamine, N-acetyl-D-galactosamine, and 2-keto-3-deoxyoctonic acid (KDO). The polysaccharides obtained by mild acid hydrolysis of the lipopolysaccharides followed by gel filtration on Sephadex G-50 were a mixture of the O-specific polysaccharide and the core, which could not be separated even by repeated rechromatography because of the comparability of their molecular masses. On the basis of the results of monosaccharide analysis, methylation, Smith degradation, and partial hydrolysis, a structure has been suggested for the repeating unit of the O-specific polysaccharides of the lipopolysaccharides ofY. enterocolitica of the serovars studied. Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, USSR Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 763–770, November–December, 1989.     

Carbohydrates of cultivated varieties ofAlthea rosea

The polysaccharides of three cultivated varieties ofAlthea rosea have been investigated. The amounts of water-soluble polysaccharides and pectin substances in various organs of the plant have been determined. It has been shown that the maximum amount of water-soluble polysaccharides and pectin substances is present in the flowers. Their monosaccharide compositions have been studied. The physicochemical characteristics of the pectin substances are given.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent. A. Sadykov Institute of Bioorganic Chemistry, Academy of Sciences of the Republic of Uzbekistan. Tashkent. Institute of Botany, Academy of Sciences of the Republic of Uzbekistan, Tashkent. Translated from Khimiya Prirodnykh Soedineii, No. 5, pp. 643–646, September–October, 1993.     

An investigation and identification of polysaccharides isolated from archeological specimens

Summary Polymeric compounds have been isolated from archeological specimens (fragments of Central Asian paintings of the 2nd-19th centuries). A comparison of their IR spectra with the spectra of plant gums has shown that they are polysaccharides which have remained undestroyed for up to 1800 yr. In some cases it has been possible from the IR spectra and composition of the extracted polysaccharides to provisionally identify sourcherry or apricot gum, of which these polysaccharides were components.All-Union Central Scientific-Research Laboratory for Conservation and Restoration, Moscow. M. M. Shemyakin Institute of Bioorganic Chemistry, Academy of Sciences of the USSR, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 15–19, January–February, 1976.