Synthesis of the pentasaccharide repeating unit of the O-antigen of Escherichia coli O175 using one-pot glycosylations and its conformational analysis

Ghosh, Tapas; Kar, Rup Kumar; Bhunia, Anirban; Misra, Anup Kumar

doi:10.1016/j.tet.2014.09.080

Tetrahedron

2014

DOI: 10.1016/j.tet.2014.09.080

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Synthesis of the pentasaccharide repeating unit of the O-antigen of Escherichia coli O175 using one-pot glycosylations and its conformational analysis

Tapas Ghosh¹,

Rup Kumar Kar²,

Anirban Bhunia³

et al.

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Cited by 2 publications

References 34 publications

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Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2013–2014

Harvey

2018

Mass Spectrometry Reviews

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This review is the eighth update of the original article published in 1999 on the application of Matrix-assisted laser desorption/ionization mass spectrometry (MALDI) mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2014. Topics covered in the first part of the review include general aspects such as theory of the MALDI process, matrices, derivatization, MALDI imaging, fragmentation, and arrays. The second part of the review is devoted to applications to various structural types such as oligo- and poly- saccharides, glycoproteins, glycolipids, glycosides, and biopharmaceuticals. Much of this material is presented in tabular form. The third part of the review covers medical and industrial applications of the technique, studies of enzyme reactions, and applications to chemical synthesis. © 2018 Wiley Periodicals, Inc. Mass Spec Rev 37:353-491, 2018.

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Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2013–2014

Harvey

2018

Mass Spectrometry Reviews

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Synthesis of the Heptasaccharide Repeating Unit of the Cell Wall O‐Polysaccharide of Enterotoxigenic Escherichia coli O139

Ghosh

Misra

2015

ChemistryOpen

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Enterotoxigenic Escherichia coli (ETEC) like the O139 strain are mostly responsible for traveler's diarrhea and causes diseases in pigs, cattle, and poultry. A convenient synthetic strategy was developed for the synthesis of the heptasaccharide repeating unit of the cell wall lipopolysaccharide of the E. coli O139 strain. The p‐methoxybenzyl (PMB) group was used as a temporary protecting group which was removed in situ under the glycosylation conditions by changing the reaction temperature during the synthesis of the target compound. All glycosylation steps gave high yields with good stereoselectivity. A (2,2,6,6‐tetramethylpiperidin‐1‐yl)oxyl (TEMPO)‐mediated selective oxidation of the primary hydroxyl group was carried out using a biphasic reaction condition at the late stage of the synthesis. Such synthetic oligosaccharides could later be effectively conjugated with proteins to prepare glycoconjugate derivatives as vaccine candidates.

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Synthesis of the pentasaccharide repeating unit of the O-antigen of Escherichia coli O175 using one-pot glycosylations and its conformational analysis

Cited by 2 publications

References 34 publications

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2013–2014

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2013–2014

Synthesis of the Heptasaccharide Repeating Unit of the Cell Wall O‐Polysaccharide of Enterotoxigenic Escherichia coli O139

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