ArticleJournal of the American Chemical Society2016
Oxidative Deamination of N-Acetyl Neuraminic Acid: Substituent Effects and Mechanism.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Concise Synthesis of Tunicamycin V and Discovery of a Cytostatic DPAGT1 Inhibitor.Angewandte Chemie (International ed. in English) · 2022Article
- Sialic Acid Derivatives Inhibit SiaT Transporters and Delay Bacterial Growth.ACS chemical biology · 2022Article
- Direct sialic acid 4-OAc substitution by nitrogen, sulfur and carbon nucleophiles with retention of stereochemistry.RSC advances · 2022Article
- Synthesis of 4-The Journal of organic chemistry · 2021Article
- 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
- 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
- Trifluoromethanesulfonate Anion as Nucleophile in Organic Chemistry.The Journal of organic chemistry · 2017Article
- Stereoselective Synthesis of the Equatorial Glycosides of Legionaminic Acid.The Journal of organic chemistry · 2017Article
- Reductive Deamination by Benzyne for Deoxy Sugar Synthesis Through a Domino Reaction.ChemistryOpen · 2017Article
- Article
- 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.The Journal of organic chemistry · 2016Article
- Oxidative deamination of amino sugars: recent advances.Carbohydrate chemistry · 1979Article
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Authors and funding
2 authors.
Funding
Abstract
A study of the mechanism of the oxidative deamination of the N-nitroso-N-acetyl sialyl glycosides leading with overall retention of configuration to the corresponding 2-keto-3-deoxy-D-glycero-D-galacto-nonulopyranosidonic acid (KDN) glycosides is described, making use of a series of differentially O-protected N-nitroso-N-acetyl sialyl glycosides and of isotopic labeling studies. No evidence is found for stereodirecting participation by ester groups at the 4- and 7-positions. Comparisons are drawn with oxidative deamination reactions of 4-amino-4-deoxy and 2-amino-2-deoxy hexopyranosides and a common mechanism is formulated involving the intermediacy of 1-oxabicyclo[3.1.0]hexyl oxonium ions following participation by the pyranoside ring oxygen. A minor reaction pathway has been uncovered by labeling studies in the β-thiosialosides that results in the exchange of the 4-O-acetyl group by the glacial acetic acid that serves as external nucleophile in the general oxidative deamination process. A mechanism is proposed for this exchange involving participation by the thioglycoside at the level of an intermediate diazoalkane.
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