ArticleJournal of the American Chemical Society2018
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.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed, 54 citations in OpenAlex.
- Selective Monoreduction of 2,4 Diazido-Dideoxy Hexoses by Hydrogenation over Lindlar Catalyst.The Journal of organic chemistry · 2025Article
- Syntheses of Legionaminic Acid, Pseudaminic Acid, Acetaminic Acid, 8-Organic letters · 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
- Side Chain Conformation Restriction in the Catalysis of Glycosidic Bond Formation by Leloir Glycosyltransferases, Glycoside Phosphorylases, and Transglycosidases.ACS catalysis · 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
- Synthesis of multiply fluorinatedBeilstein journal of organic chemistry · 2021Article
- Synthesis of 3-Deoxy-d-The Journal of organic chemistry · 2020Article
- 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
- Direct, stereoselective thioglycosylation enabled by an organophotoredox radical strategy.Chemical science · 2020Article
- Glycoside Hydrolases Restrict the Side Chain Conformation of Their Substrates To Gain Additional Transition State Stabilization.Journal of the American Chemical Society · 2020Article
- Recent progress in chemical synthesis of bacterial surface glycans.Current opinion in chemical biology · 2020Review
- Transfer learning enables the molecular transformer to predict regio- and stereoselective reactions on carbohydrates.Nature communications · 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 of saccharocin from apramycin and evaluation of its ribosomal selectivity.MedChemComm · 2019Article
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2 authors at 1 institution in 1 country.
Funding
Abstract
Pseudaminic acid is an amino deoxy sialic acid whose glycosides are essential components of many pathogenic Gram-negative bacterial cell walls including those from Pseudomonas aeruginosa, Vibrio cholerae, Campylobacter jejuni, Campylobacter coli, Vibrio vulnificus, and Pseudoalteromonas distincta. The study of pseudaminic acid glycosides is however hampered by poor availability from nature and the paucity of good synthetic methods and limited to no understanding of the factors controlling stereoselectivity. Conformational analysis of the side chains of various stereoisomeric sialic acids suggested that the side chain of pseudaminic acid would take up the most electron-withdrawing trans, gauche-conformation, as opposed to the gauche, gauche conformation of N-acetyl neuraminic acid and the gauche, trans-conformtion of 7- epi N-acetyl neuraminic acid, leading to the prediction of high equatorial selectivity. This prediction is borne out by the synthesis of a suitably protected pseudaminic acid donor from N-acetyl neuraminic acid in 20 steps and 5% overall yield and by the exquisite equatorial selectivity it displays in coupling reactions with typical glycosyl acceptors. The selectivity of the glycosylation reactions is further buttressed by the development and implementation of conditions for the regioselective release of the two amines from the corresponding azides, such as required for the preparation of the lipopolysaccharides. These findings open the way to the synthesis and study of pseudaminic acid-based bacterial lipopolysaccharides and, importantly in the broader context of glycosylation reactions in general, underline the significant role played by side-chain conformation in the control of reactivity and selectivity.
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