Convergent synthesis of the pentasaccharide repeating unit of the O-antigenic polysaccharide of enterohaemorrhagic Escherichia coli O113

Santra, Abhishek; Misra, Anup Kumar

doi:10.1007/s10719-012-9383-4

Cited by 3 publications

(1 citation statement)

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“…baumannii K11 is presented as its p -methoxyphenyl (PMP) glycoside. The PMP group could act as a stable and oxidatively cleavable anomeric protecting group . This property makes the group available for removal on demand, making it convenient to use.…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of 6-Deoxy-l-talose Containing a Pentasaccharide Repeating Unit of Acinetobacter baumannii K11 Capsular Polysaccharides

Bharali

Santra

2023

J. Org. Chem.

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Herein, we report a concise synthetic approach for the first total synthesis of a pentasaccharide repeating unit of Acinetobacter baumannii K11 capsular polysaccharides containing a rare sugar 6-deoxy-L-talose. The pentasaccharide was synthesized in a convergent manner using a [3 + 2] block glycosylation strategy. During this synthetic strive, we used a 2,2,2trichloroethoxycarbonyl (Troc)-protected monosaccharide unit to achieve a high yield during the glycosylation to synthesize a trisaccharide, and chemoselective deprotection of the Troc group from the trisaccharide was carried out under a mild, pH-neutral condition, keeping the O-glycosidic bond, azido, and acid/base sensitive group intact. A thiotolylglycoside disaccharide donor containing 6-deoxy-L-talose was synthesized for the first time by the armed-disarmed glycosylation method between two thiotolylglycosides.

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Section: Introductionmentioning

confidence: 99%

Total Synthesis of 6-Deoxy-l-talose Containing a Pentasaccharide Repeating Unit of Acinetobacter baumannii K11 Capsular Polysaccharides

Bharali

Santra

2023

J. Org. Chem.

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Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2011–2012

Harvey

2015

Mass Spectrometry Reviews

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This review is the seventh update of the original article published in 1999 on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2012. General aspects such as theory of the MALDI process, matrices, derivatization, MALDI imaging, and fragmentation are covered in the first part of the review and applications to various structural types constitute the remainder. The main groups of compound are oligo- and poly-saccharides, glycoproteins, glycolipids, glycosides, and biopharmaceuticals. Much of this material is presented in tabular form. Also discussed are medical and industrial applications of the technique, studies of enzyme reactions, and applications to chemical synthesis. © 2015 Wiley Periodicals, Inc. Mass Spec Rev 36:255-422, 2017.

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Synthesis of oligosaccharides related to cell wall polysaccharides of the fungi Candida and Aspergillus

Karelin¹,

Tsvetkov²,

Nifantiev³

2017

Russ. Chem. Rev.

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Convergent synthesis of the pentasaccharide repeating unit of the O-antigenic polysaccharide of enterohaemorrhagic Escherichia coli O113

Cited by 3 publications

References 35 publications

Total Synthesis of 6-Deoxy-l-talose Containing a Pentasaccharide Repeating Unit of Acinetobacter baumannii K11 Capsular Polysaccharides

Total Synthesis of 6-Deoxy-l-talose Containing a Pentasaccharide Repeating Unit of Acinetobacter baumannii K11 Capsular Polysaccharides

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2011–2012

Synthesis of oligosaccharides related to cell wall polysaccharides of the fungi Candida and Aspergillus

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