Convergent synthesis of the hexasaccharide related to the repeating unit of the O-antigen from E. coli O120

Budhadev, Darshita; Mukhopadhyay, Balaram

doi:10.1039/c5ra20363e

Cited by 6 publications

(3 citation statements)

References 29 publications

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“…The a-(1/2) linked L-rhamnose motif is a fairly common oligosaccharide architecture which has been synthesised by our group previously. 8,9 This was selected as the rst point of retrosynthetic disconnection in contemplation of a (3+1+1) convergent strategy for oligosaccharide assembly.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of the pentasaccharide repeating unit of the O-antigen from Enterobacter cloacae C4115 containing the rare α-d-FucNAc

Chaudhury

Mukhopadhyay

2020

RSC Adv.

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Section: Resultsmentioning

confidence: 99%

Synthesis of the pentasaccharide repeating unit of the O-antigen from Enterobacter cloacae C4115 containing the rare α-d-FucNAc

Chaudhury

Mukhopadhyay

2020

RSC Adv.

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“…Another strategy has been to produce polysaccharides synthetically in blocks. The exact number can vary, such as a di-and tetra-saccharides (Budhadev & Mukhopadhyay, 2015), di-and tri-saccharides (Mandal, 2014;Mondal, Liao, Mondal, & Guo, 2015;Si & Misra, 2016), three disaccharides (Scott et al, 2016) and two tri-saccharides (Seeberger, Pereira, & Govindan, 2017). However, it should be noted that it is possible to compare assembly methods and one study revealed that linear assembly may be more effective than block assembly (Dhara & Misra, 2015;Seeberger et al, 2017).…”

Section: Polysaccharide Productionmentioning

confidence: 99%

Glycoconjugate vaccines: some observations on carrier and production methods

MacCalman

Phillips‐Jones

Harding

2019

Biotechnology and Genetic Engineering Reviews

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Glycoconjugate vaccines use protein carriers to improve the immune response to polysaccharide antigens. The protein component allows the vaccine to interact with T cells, providing a stronger and longer-lasting immune response than a polysaccharide interacting with B cells alone. Whilst in theory the mere presence of a protein component in a vaccine should be sufficient to improve vaccine efficacy, the extent of improvement varies. In the present review, a comparison of the performances of vaccines developed with and without a protein carrier are presented. The usefulness of analytical tools for macromolecular integrity assays, in particular nuclear magnetic resonance, circular dichroism, analytical ultracentrifugation and SEC coupled to multi-angle light scattering (MALS) is indicated. Although we focus mainly on bacterial capsular polysaccharideprotein vaccines, some consideration is also given to research on experimental cancer vaccines using zwitterionic polysaccharides which, unusually for polysaccharides, are able to invoke T-cell responses and have been used in the development of potential all-polysaccharide-based cancer vaccines.A general trend of improved immunogenicity for glycoconjugate vaccines is described. Since the immunogenicity of a vaccine will also depend on carrier protein type and the way in which it has been linked to polysaccharide, the effects of different carrier proteins and production methods are also reviewed. We suggest that, in general, there is no single best carrier for use in glycoconjugate vaccines. This indicates that the choice of carrier protein is optimally made on a case-by-case basis, based on what generates the best immune response and can be produced safely in each individual case.

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“…Synthesis of an oligosaccharide with a temporary protecting group at the reducing end would be useful for its easy removal whenever necessary as it is often required to attach the oligosaccharide with a carrier protein through a spacer linker toward synthesis of glycoconjugates . In this direction, the synthesis of the oligosaccharide related to the repeating unit of the O -antigen from E. coli 120 was only reported by Mukhopadhyay et al, using a conventional stepwise approach. However, introduction of a step-economic multistep, one-pot total synthesis is still necessary and needs refinement of the entire synthetic protocol.…”

Section: Introductionmentioning

confidence: 99%

Synthetic Routes toward Acidic Pentasaccharide Related to the O-Antigen of E. coli 120 Using One-Pot Sequential Glycosylation Reactions

Mukherjee

Ghosh

2017

J. Org. Chem.

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Concise syntheses of the acidic pentasaccharide, related to the O-antigenic polysaccharide of Escherichia coli 120, as its p-methoxyphenyl glycoside, have been achieved using a one-pot sequential glycosylation technique. The glycosylations have been accomplished either by the activation of the thioglycosides using NIS in the presence of FeCl or by a preactivation by PhSO, TTBP, TfO, and the activation of the trichloroacetimidates using FeCl alone or TMSOTf. Most of the intermediate steps are high yielding, and the stereo outcomes of the glycosylation steps were excellent. The syntheses of the targeted pentasaccharide have been performed with both three- and four-component, one-pot sequential glycosylation reactions, and in both cases, the orthogonal glycosylations are carried out utilizing catalytic activity of FeCl. A late-stage TEMPO-mediated regioselective oxidation has been performed to achieve the required uronic acid motif.

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Convergent synthesis of the hexasaccharide related to the repeating unit of the O-antigen from E. coli O120

Abstract: The hexasaccharide repeating unit of the O-antigen from E. coli O120 has been synthesized in the form of its 4-methoxyphenyl glycoside by a convergent [2 + 4] strategy.

Cited by 6 publications

References 29 publications

Synthesis of the pentasaccharide repeating unit of the O-antigen from Enterobacter cloacae C4115 containing the rare α-d-FucNAc

Synthesis of the pentasaccharide repeating unit of the O-antigen from Enterobacter cloacae C4115 containing the rare α-d-FucNAc

Glycoconjugate vaccines: some observations on carrier and production methods

Synthetic Routes toward Acidic Pentasaccharide Related to the O-Antigen of E. coli 120 Using One-Pot Sequential Glycosylation Reactions

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