Synthesis of a Glycosylphosphatidylinositol Anchor Derived from <i>Leishmania donovani</i> That Can Be Functionalized by Cu-Catalyzed Azide–Alkyne Cycloadditions

Ding, Ning; Li, Xiuru; Chinoy, Zoeisha S.; Boons, Geert‐Jan

doi:10.1021/acs.orglett.7b01703

Cited by 20 publications

(10 citation statements)

References 31 publications

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“…In the course of our synthetic studies on glycoprobes, − we became involved in the synthesis of enol glycosides. Here, we now report our recent work on the direct glycosylation of a ketone with an O -glycosyl trichloroacetimidate under typical glycosylation conditions.…”

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confidence: 60%

Glycosylation of a Ketone with an O-Glycosyl Trichloroacetimidate Provides an Enol Glycoside

et al. 2018

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An enol-type glycosylation reaction has been investigated. Enol glycosides can be obtained from the reaction between O-glycosyl trichloroacetimidates and the corresponding ketones promoted by an acid. The enol glycosides derived from cyclic ketones can be afforded efficiently and isolated in good yield, while those from acyclic ketones are prepared in low conversion or are too labile for isolation. Further studies on different glycosyl donor types indicate that only the O-glycosyl trichloroacetimidate works well as a donor for enol glycosylation.

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confidence: 60%

Glycosylation of a Ketone with an O-Glycosyl Trichloroacetimidate Provides an Enol Glycoside

et al. 2018

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“…It also ensured a minimal number of deprotection steps, using hydroxyl masking groups orthogonal to allyl, trichloroacetamide, and CA. A strategy still barely adopted in oligosaccharide synthesis, although it has met some success in the synthesis of demanding glycolipids bearing unsaturated lipid chains − and is the subject of increasing interest, was favored. It involves a panel of protecting groups compatible with acid-mediated removal.…”

Section: Results and Discussionmentioning

confidence: 99%

Convergent Chemoenzymatic Strategy to Deliver a Diversity of Shigella flexneri Serotype-Specific O-Antigen Segments from a Unique Lightly Protected Tetrasaccharide Core

Benkoulouche

Barel

et al. 2020

J. Org. Chem.

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HAL is a multi-disciplinary open access archive for the deposit and dissemination of scientific research documents, whether they are published or not. The documents may come from teaching and research institutions in France or abroad, or from public or private research centers. L'archive ouverte pluridisciplinaire HAL, est destinée au dépôt et à la diffusion de documents scientifiques de niveau recherche, publiés ou non, émanant des établissements d'enseignement et de recherche français ou étrangers, des laboratoires publics ou privés.Distributed under a Creative Commons Attribution -NonCommercial| 4.0 International License

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“…The synthesis of trilipidated pseudodisaccharide 4 required the synthesis of a modified pseudodisaccharide having an orthogonal group at the 2-O position of inositol. 38 The process started with the glycosylation of inositol 15 ( 38 ) with glycosyl imidate 14 by TMSOTf activation to obtain a pseudodisaccharide. Following deacetylation with sodium methoxide in methanol and etherification with 2-naphthylmethyl bromide delivered the protected pseudodisaccharide 16 in 61% yield over the three steps.…”

Section: Resultsmentioning

confidence: 99%

Rescue of Glycosylphosphatidylinositol-Anchored Protein Biosynthesis Using Synthetic Glycosylphosphatidylinositol Oligosaccharides

et al. 2021

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The attachment of proteins to the cell membrane using a glycosylphosphatidylinositol (GPI) anchor is a ubiquitous process in eukaryotic cells. Deficiencies in the biosynthesis of GPIs and the concomitant production of GPI-anchored proteins lead to a series of rare and complicated disorders associated with inherited GPI deficiencies (IGDs) in humans. Currently, there is no treatment for patients suffering from IGDs. Here, we report the design, synthesis, and use of GPI fragments to rescue the biosynthesis of GPI-anchored proteins (GPI-APs) caused by mutation in genes involved in the assembly of GPI-glycolipids in cells. We demonstrated that the synthetic fragments GlcNAc-PI ( 1 ), Man-GlcN-PI ( 5 ), and GlcN-PI with two ( 3 ) and three lipid chains ( 4 ) rescue the deletion of the GPI biosynthesis in cells devoid of the PIGA, PIGL, and PIGW genes in vitro. The compounds allowed for concentration-dependent recovery of GPI biosynthesis and were highly active on the cytoplasmic face of the endoplasmic reticulum membrane. These synthetic molecules are leads for the development of treatments for IGDs and tools to study GPI-AP biosynthesis.

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Synthesis of a Glycosylphosphatidylinositol Anchor Derived from Leishmania donovani That Can Be Functionalized by Cu-Catalyzed Azide–Alkyne Cycloadditions

Cited by 20 publications

References 31 publications

Glycosylation of a Ketone with an O-Glycosyl Trichloroacetimidate Provides an Enol Glycoside

Glycosylation of a Ketone with an O-Glycosyl Trichloroacetimidate Provides an Enol Glycoside

Convergent Chemoenzymatic Strategy to Deliver a Diversity of Shigella flexneri Serotype-Specific O-Antigen Segments from a Unique Lightly Protected Tetrasaccharide Core

Rescue of Glycosylphosphatidylinositol-Anchored Protein Biosynthesis Using Synthetic Glycosylphosphatidylinositol Oligosaccharides

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