scholarly journals Synthesis of Pentasaccharide Repeating Unit Corresponding to the Cell Wall O-Polysaccharide of Salmonella enterica O55 Strain Containing a Rare Sugar 3-Acetamido-3-deoxy-d-fucose

Synthesis ◽  
2021 ◽  
Author(s):  
Anup Kumar Misra ◽  
Arin Gucchait ◽  
Monalisa Kundu
Keyword(s):  
Cell Wall ◽  
Salmonella Enterica ◽  
Good Yield ◽  
Rare Sugar ◽  
Stereoselective Glycosylation ◽  
O Antigen ◽  
Excellent Yield ◽  
Glycosylation Reaction

AbstractA pentasaccharide repeating unit corresponding to the cell wall O-antigen of Salmonella enterica O55 containing a rare sugar, 3-acetamido-3-deoxy-d-fucose has been synthesized as its p-methoxyphenyl glycoside using a sequential stereoselective glycosylation strategy. A suitably functionalized 3-azido-3-deoxy-d-fucose thioglycoside derivative was prepared in very good yield and used in the stereoselective glycosylation reaction. Functionalized monosaccharide intermediates were prepared judiciously and stereoselectively assembled to get the desired pentasaccharide derivative in excellent yield.

scholarly journals Convenient synthesis of the pentasaccharide repeating unit corresponding to the cell wall O-antigen of Escherichia albertii O4

2020 ◽  
Vol 16 ◽  
pp. 106-110 ◽  
Author(s):  
Tapasi Manna ◽  
Arin Gucchait ◽  
Anup Kumar Misra
Keyword(s):  
Cell Wall ◽  
Perchloric Acid ◽  
Good Yield ◽  
Protecting Groups ◽  
O Antigen ◽  
Synthetic Strategy ◽  
Convenient Synthesis ◽  
Selection Of ◽  
Glycosyl Donors

A straightforward sequential synthetic strategy has been developed for the synthesis of a pentasaccharide repeating unit corresponding to the cell wall O-antigen of the Escherichia albertii O4 strain in very good yield with the desired configuration at the glycosidic linkages using thioglycosides and trichloroacetimidate derivatives as glycosyl donors and perchloric acid supported over silica (HClO4/SiO2) as a solid supported protic acid glycosyl activator. The expected configuration at the glycosidic linkages was achieved using a reasonable selection of protecting groups in the manosaccharide intermediates.

Concise synthesis of a tetrasaccharide related to the repeating unit of the cell wall O-antigen of Salmonella enterica O60

Tetrahedron ◽  
2020 ◽  
Vol 76 (34) ◽  
pp. 131412 ◽  
Author(s):  
Arin Gucchait ◽  
Pradip Shit ◽  
Anup Kumar Misra
Keyword(s):  
Cell Wall ◽  
Salmonella Enterica ◽  
O Antigen

scholarly journals Relationships among the O-Antigen Gene Clusters ofSalmonella enterica Groups B, D1, D2, and D3

1998 ◽  
Vol 180 (4) ◽  
pp. 1002-1007 ◽  
Author(s):  
Heather Curd ◽  
Dan Liu ◽  
Peter R. Reeves
Keyword(s):  
Cell Wall ◽  
Gene Cluster ◽  
Salmonella Enterica ◽  
Sequence Similarity ◽  
Gene Clusters ◽  
Gram Negative Bacteria ◽  
Polymerase Gene ◽  
Gram Negative ◽  
Antigen Gene ◽  
O Antigen

ABSTRACT The O antigen is an important cell wall antigen of gram-negative bacteria, and the genes responsible for its biosynthesis are located in a gene cluster. We have cloned and sequenced the DNA segment unique to the O-antigen gene cluster of Salmonella enterica group D3. This segment includes a novel O-antigen polymerase gene (wzy D3). The polymerase gives α(1→6) linkages but has no detectable sequence similarity to that of group D2, which confers the same linkage. We find the remnant of a D3-likewzy gene in the O-antigen gene clusters of groups D1 and B and suggest that this is the original wzy gene of these O-antigen gene clusters.

scholarly journals Association of a Protective Monoclonal IgA with the O Antigen of Salmonella enterica Serovar Typhimurium Impacts Type 3 Secretion and Outer Membrane Integrity

2012 ◽  
Vol 80 (7) ◽  
pp. 2454-2463 ◽  
Author(s):  
Stephen J. Forbes ◽  
Daniel Martinelli ◽  
Chyongere Hsieh ◽  
Jeffrey G. Ault ◽  
Michael Marko ◽  
...  
Keyword(s):  
Electron Microscopy ◽  
Epithelial Cells ◽  
Outer Membrane ◽  
Salmonella Enterica ◽  
Membrane Integrity ◽  
Effector Proteins ◽  
Content Type ◽  
O Antigen ◽  
Serovar Typhimurium ◽  
Type 3

ABSTRACTInvasion of intestinal epithelial cells bySalmonella entericaserovar Typhimurium is an energetically demanding process, involving the transfer of effector proteins from invading bacteria into host cells via a specialized organelle known as theSalmonellapathogenicity island 1 (SPI-1) type 3 secretion system (T3SS). By a mechanism that remains poorly understood, entry ofS. Typhimurium into epithelial cells is inhibited by Sal4, a monoclonal, polymeric IgA antibody that binds an immunodominant epitope within the O-antigen (O-Ag) component of lipopolysaccharide. In this study, we investigated how the binding of Sal4 to the surface ofS. Typhimurium influences T3SS activity, bacterial energetics, and outer membrane integrity. We found that Sal4 treatment impaired T3SS-mediated translocon formation and attenuated the delivery of tagged effector proteins into epithelial cells. Sal4 treatment coincided with a partial reduction in membrane energetics and intracellular ATP levels, possibly explaining the impairment in T3SS activity. Sal4's effects on bacterial secretion and energetics occurred concurrently with an increase in O-Ag levels in culture supernatants, alterations in outer membrane permeability, and changes in surface ultrastructure, as revealed by transmission electron microscopy and cryo-electron microscopy. We propose that Sal4, by virtue of its ability to bind and cross-link the O-Ag, induces a form of outer membrane stress that compromises the integrity of theS. Typhimurium cell envelope and temporarily renders the bacterium avirulent.

Structural and genetic characterization of the O-antigen of Salmonella enterica O56 containing a novel derivative of 4-amino-4,6-dideoxy-d-glucose

2010 ◽  
Vol 345 (13) ◽  
pp. 1891-1895 ◽  
Author(s):  
Andrei V. Perepelov ◽  
Bin Liu ◽  
Sergei D. Shevelev ◽  
Sof’ya N. Senchenkova ◽  
Bo Hu ◽  
...  
Keyword(s):  
Salmonella Enterica ◽  
Genetic Characterization ◽  
O Antigen
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