ArticleThe Journal of organic chemistry2016
Stereoselective Synthesis of 5-epi-α-Sialosides Related to the Pseudaminic Acid Glycosides. Reassessment of the Stereoselectivity of the 5-Azido-5-deacetamidosialyl Thioglycosides and Use of Triflate as Nucleophile in the Zbiral Deamination of Sialic Acids.
Article in The Journal of organic chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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Who cites it
24 citing papers in PubMed.
- Total Synthesis of the SJG-2 Glycan: General Strategies for Constructing Sterically Congested Sialylated Glycans.Journal of the American Chemical Society · 2026Article
- Broad-Spectrum Legionaminic Acid-Specific Antibodies in Pooled Human IgGs Revealed by Glycan Microarrays with Chemoenzymatically Synthesized Nonulosonosides.Molecules (Basel, Switzerland) · 2024Article
- A cell free biomembrane platform for multimodal study of influenza virus hemagglutinin and for evaluation of entry-inhibitors against hemagglutinin.Frontiers in molecular biosciences · 2022Article
- Influence of Configuration at the 4- and 6-Positions on the Conformation and Anomeric Reactivity and Selectivity of 7-Deoxyheptopyranosyl Donors: Discovery of a Highly Equatorially Selective l-The Journal of organic chemistry · 2021Article
- GH47 and Other Glycoside Hydrolases Catalyze Glycosidic Bond Cleavage with the Assistance of Substrate Super-arming at the Transition State.ACS catalysis · 2021Article
- Azide-Functionalized Derivatives of the Virulence-Associated Sugar Pseudaminic Acid: Chiral Pool Synthesis and Labeling of Bacteria.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- An efficient and scalable synthesis of 2,4-di-RSC advances · 2021Article
- Influence of substitution at the 5α-Position on the side chain conformation of glucopyranosides.Carbohydrate research · 2021Article
- En Route to the Transformation of Glycoscience: A Chemist's Perspective on Internal and External Crossroads in Glycochemistry.Journal of the American Chemical Society · 2021Article
- Predictive Analysis of the Side Chain Conformation of the Higher Carbon Sugars: Application to the Preorganization of the Aminoglycoside Ring 1 Side Chain for Binding to the Bacterial Ribosomal Decoding A Site.The Journal of organic chemistry · 2020Article
- Glycoside Hydrolases Restrict the Side Chain Conformation of Their Substrates To Gain Additional Transition State Stabilization.Journal of the American Chemical Society · 2020Article
- Influence of protecting groups on O- and C-glycosylation with neuraminyl and ulosonyl dibutylphosphates.Carbohydrate research · 2020Article
- Mechanisms of Stereodirecting Participation and Ester Migration from Near and Far in Glycosylation and Related Reactions.Chemical reviews · 2020Article
- Stereocontrolled Synthesis of the Equatorial Glycosides of 3-Deoxy-d-manno-oct-2-ulosonic Acid: Role of Side Chain Conformation.Journal of the American Chemical Society · 2020Article
- Use of hydroxylamines, hydroxamic acids, oximes and amines as nucleophiles in the Zbiral oxidative deamination of N-acetyl neuraminic acid. Isolation and characterization of novel mono- and disubstitution products.Carbohydrate research · 2020Article
- Use of Phenols as Nucleophiles in the Zbiral Oxidative Deamination ofThe Journal of organic chemistry · 2019Article
- Synthesis and Immunological Evaluation of Disaccharide Bearing MUC-1 Glycopeptide Conjugates with Virus-like Particles.ACS chemical biology · 2019Article
- Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity.MedChemComm · 2019Article
- Synthesis and Stereocontrolled Equatorially Selective Glycosylation Reactions of a Pseudaminic Acid Donor: Importance of the Side-Chain Conformation and Regioselective Reduction of Azide Protecting Groups.Journal of the American Chemical Society · 2018Article
- The Experimental Evidence in Support of Glycosylation Mechanisms at the SChemical reviews · 2018Review
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3 authors.
Funding
Abstract
With a view to the eventual synthesis of glycosyl donors for the stereocontrolled synthesis of pseudaminic acid glycosides, the stereocontrolled synthesis of a d-glycero-d-gulo sialic acid adamantanylthioglycoside carrying an axial azide at the 5-position is described. The synthesis employs levulinic acid as nucleophile in the oxidative deamination of an N-acetylneuraminic acid thioglycoside leading to the formation of a 3-deoxy-d-glycero-d-galacto-2-nonulosonic acid (KDN) derivative selectively protected as 5-O-levulinate. Replacement of the levulinate by triflate enables introduction of the axial azide and hence formation of the glycosyl donor. A shorter synthesis uses trifluoromethanesulfonate as nucleophile in the oxidative deamination step when the 5-O-triflyl KDN derivative is obtained directly. Glycosylation reactions conducted with the 5-azido-d-glycero-d-gulo-configured sialyl adamantanylthioglycoside at -78 °C are selective for the formation of the equatorial glycosides, suggesting that the synthesis of equatorial pseudaminic acid glycosides will be possible as suitable donors become available. A comparable N-acetylneuraminic acid adamantanylthioglycoside carrying an equatorial azide at the 5-position was also found to be selective for equatorial glycoside formation under the same conditions, suggesting that reinvestigation of other azide-protected NeuAc donors is merited. Glycosylation stereoselectivity in the d-glycero-d-gulo series is discussed in terms of the side-chain conformation of the donor.
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