Structure elucidation and gene cluster characterization of the O-antigen of Escherichia coli O80

Senchenkova, Sof’ya N.; Guo, Xi; Filatov, Andrei V.; Liu, Bin; Shashkov, Alexander S.; Knirel, Yuriy A.

doi:10.1016/j.carres.2016.07.011

Carbohydrate Research

2016

DOI: 10.1016/j.carres.2016.07.011

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Structure elucidation and gene cluster characterization of the O-antigen of Escherichia coli O80

Sof’ya N. Senchenkova

Xi Guo

Andrei V. Filatov

et al.

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Cited by 3 publications

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“…The structure of the repeating unit of the O -antigen of E. coli O80 has been reported by Knirel and co-workers. 11 The hexasaccharide repeating unit is composed of two α-linked l -fucose, N -acetyl-β- d -glucosamine, N -acetyl-β- d -galactosamine, β- d -glucose, and β- d -glucuronic acid moieties. Obtaining the oligosaccharides from natural sources by applying fermentation technology suffers from a number of shortcomings, such as insufficient yield, lack of homogeneity, chances of contamination with biological impurities, e.g.…”

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confidence: 99%

Convenient Synthesis of the Branched Hexasaccharide Repeating Unit of the Cell Wall O-Antigen of Escherichia coli O80 Strain

Misra,

Sahaji

2023

Synthesis

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Chemical synthesis of a branched hexasaccharide corresponding to the cell wall O-antigen of Escherichia coli (E. coli) O80 strain has been achieved in very good yield with satisfactory stereochemical outcome around the glycosidic linkages by applying a regio- and stereoselective [4+2] block glycosylation strategy. The tetrasaccharide diol derivative was synthesized from suitably functionalized monosaccharide intermediates using sequential stereoselective glycosylations and the disaccharide thioglycoside donor was obtained applying a regio- and stereoselective orthogonal armed-disarmed glycosylation strategy using protected thioglycoside derivatives. A late-stage TEMPO and bis(acetoxy)iodobenzene (BAIB) mediated regioselective oxidation of the primary hydroxyl group of the protected hexasaccharide derivative to the carboxylic acid was achieved leaving secondary hydroxyl groups unaffected.

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mentioning

confidence: 99%

Convenient Synthesis of the Branched Hexasaccharide Repeating Unit of the Cell Wall O-Antigen of Escherichia coli O80 Strain

Misra,

Sahaji

2023

Synthesis

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Chemical methods for selective cleavage of glycosidic bonds in the structural analysis of bacterial polysaccharides

Knirel¹,

Naumenko²,

Senchenkova³

et al. 2019

Russ. Chem. Rev.

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This review is devoted to methods for the selective cleavage of glycosidic bonds. The mechanisms of reactions underlying these methods are considered and examples of their practical application in the structural analysis of bacterial polysaccharides are given. Specific methods for the selective cleavage of polysaccharides, remaining relevant for researchers, include the Smith degradation based on destruction of monosaccharides containing vicinal diol groups, dephosphorylation of phosphate-containing polysaccharides with hydrofluoric acid and the hydrolytic cleavage of glycosyl phosphate bonds in the latter compounds. Non-specific methods, including partial acid hydrolysis, acetolysis and solvolysis with anhydrous organic (CF3SO3H, MeSO3H, CF3CO2H) and inorganic (HF) acids do not make any specific demands on the composition and structure of the polysaccharide and are sensitive to its fine structural features. The review addesses the issue of stability of glycosidic bonds in various monosaccharides to reagents used for non-specific selective cleavage. The bibliography includes 58 references.

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Structure and genetics ofEscherichia coliO antigens

Liu

Furevi

Perepelov

et al. 2019

FEMS Microbiology Reviews

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184

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Escherichia coli includes clonal groups of both commensal and pathogenic strains, with some of the latter causing serious infectious diseases. O antigen variation is current standard in defining strains for taxonomy and epidemiology, providing the basis for many serotyping schemes for Gram-negative bacteria. This review covers the diversity in E. coli O antigen structures and gene clusters, and the genetic basis for the structural diversity. Of the 187 formally defined O antigens, six (O31, O47, O67, O72, O94 and O122) have since been removed and four (O14, O34, O89 and O144) strains do not produce any O antigen. Therefore, structures are presented for 176 of the 181 E. coli O antigens, some of which include subgroups. Most (93%) of these O antigens are synthesized via the Wzx/Wzy pathway, 11 via the ABC transporter pathway, with O20, O57 and O60 still uncharacterized due to failure to find their O antigen gene clusters. Biosynthetic pathways are given for 38 of the 49 sugars found in E. coli O antigens, and several pairs or groups of the E. coli antigens that have related structures show close relationships of the O antigen gene clusters within clades, thereby highlighting the genetic basis of the evolution of diversity.

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Structure elucidation and gene cluster characterization of the O-antigen of Escherichia coli O80

Cited by 3 publications

References 12 publications

Convenient Synthesis of the Branched Hexasaccharide Repeating Unit of the Cell Wall O-Antigen of Escherichia coli O80 Strain

Convenient Synthesis of the Branched Hexasaccharide Repeating Unit of the Cell Wall O-Antigen of Escherichia coli O80 Strain

Chemical methods for selective cleavage of glycosidic bonds in the structural analysis of bacterial polysaccharides

Structure and genetics ofEscherichia coliO antigens

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