Expeditious synthesis of the tetrasaccharide cap domain of the Leishmania donovani lipophosphoglycan using one-pot glycosylation reactions

Mukherjee, M.; Basu, Nabamita; Ghosh, Rina

doi:10.1039/c6ra03856e

Cited by 7 publications

(1 citation statement)

References 41 publications

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“…For the synthesis of tetrasaccharides with only a-1,3 or a-1,6branch, the disaccharide 37 was rst synthesized by coupling of donor 21 with the known acceptor 36. 37 Aer the conversion of the benzoyl group to permanent benzyl group, the resulting disaccharide 38 was then used as the glycosyl donor for coupling with 20 under the promotion of NIS and TfOH to provide 39 in 74% yield, which was conrmed as the sole a isomer. Aer reduction of the azido group to acetamido group, followed by the selective deprotection of TIPS group, the C6 free OH was phosphorylated to give 42.…”

Section: Resultsmentioning

confidence: 99%

Chemoenzymatic glycan-selective remodeling of a therapeutic lysosomal enzyme with high-affinity M6P-glycan ligands. Enzyme substrate specificity is the name of the game

et al. 2021

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Section: Resultsmentioning

confidence: 99%

Chemoenzymatic glycan-selective remodeling of a therapeutic lysosomal enzyme with high-affinity M6P-glycan ligands. Enzyme substrate specificity is the name of the game

et al. 2021

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Synthesis of Fluorinated Leishmania Cap Trisaccharides for Diagnostic Tool and Vaccine Development

et al. 2018

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Bearing in mind the often insufficient metabolic stability of carbohydrate antigens, which impairs both the bioavailability and immunogenicity of a given hapten, the development of chemically modified analogs with improved antigenicity is an important step towards effective glycoconjugate vaccines. Recently, strategic glycan fluorination has become an interesting approach to this, and several examples of fluorinated carbohydrate antigens that show better metabolic stabilities and comparable or even enhanced immunogenicities have been reported to date. In this paper, we present a small library of fluorinated trisaccharides based on a privileged motif from the lipophosphoglycan capping structure of Leishmania donovani, a protozoan parasite responsible for fatal visceral leishmaniasis. These epitope analogs were synthesized by a sequential [1+1+1] glycosylation strategy. An amine linker is present at the reducing end to allow conjugation and enable future applications in immunological studies for the development of diagnostic tools and vaccines.

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Leishmania lipophosphoglycan components: A potent target for synthetic neoglycoproteins as a vaccine candidate for leishmaniasis

Mohammed

Tian

Zhang

et al. 2020

Carbohydrate Polymers

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Expeditious synthesis of the tetrasaccharide cap domain of the Leishmania donovani lipophosphoglycan using one-pot glycosylation reactions

Abstract: Expeditious syntheses of the tetrasaccharide cap related to the lipophosphoglycan ofLeishmania donovaniwere achieved by sequential one-pot glycosylation reactions.

Cited by 7 publications

References 41 publications

Chemoenzymatic glycan-selective remodeling of a therapeutic lysosomal enzyme with high-affinity M6P-glycan ligands. Enzyme substrate specificity is the name of the game

Chemoenzymatic glycan-selective remodeling of a therapeutic lysosomal enzyme with high-affinity M6P-glycan ligands. Enzyme substrate specificity is the name of the game

Synthesis of Fluorinated Leishmania Cap Trisaccharides for Diagnostic Tool and Vaccine Development

Leishmania lipophosphoglycan components: A potent target for synthetic neoglycoproteins as a vaccine candidate for leishmaniasis

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