ArticleThe Journal of organic chemistry2020
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.
Article in The Journal of organic chemistry, 2020. 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.
- Synthesis, Conformational Analysis, and Evaluation of 6ACS omega · 2026Article
- Unnatural C6-Substituted d-Galactosides as Attenuated Substrates of Glycosyl Hydrolases.Chembiochem : a European journal of chemical biology · 2026Article
- Stereochemistry-dependent thermotropic liquid crystalline phases of monosaccharide-based amphiphiles.Soft matter · 2023Article
- Synthesis of Gentamicins C1, C2, and C2a and Antiribosomal and Antibacterial Activity of Gentamicins B1, C1, C1a, C2, C2a, C2b, and X2.ACS infectious diseases · 2023Article
- Can Side-Chain Conformation and Glycosylation Selectivity of Hexopyranosyl Donors Be Controlled with a Dummy Ligand?The Journal of organic chemistry · 2023Article
- Influence of Side Chain Conformation on the Activity of Glycosidase Inhibitors.Angewandte Chemie (International ed. in English) · 2023Article
- Syntheses of Legionaminic Acid, Pseudaminic Acid, Acetaminic Acid, 8-Organic letters · 2022Article
- Side Chain Conformation and Its Influence on Glycosylation Selectivity in Hexo- and Higher Carbon Furanosides.The Journal of organic chemistry · 2022Article
- Unusual C-C bond cleavage of an α-trifloxy Sialic acid hemiacetal under Lattrell-Dax conditions.Carbohydrate research · 2022Article
- Influence of ring size in conformationally restricted ring I analogs of paromomycin on antiribosomal and antibacterial activity.RSC medicinal chemistry · 2021Article
- 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
- Side Chain Conformation Restriction in the Catalysis of Glycosidic Bond Formation by Leloir Glycosyltransferases, Glycoside Phosphorylases, and Transglycosidases.ACS catalysis · 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
Corrections and comments
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Authors and funding
6 authors.
Funding
Abstract
With a view to facilitating prediction of the exocyclic bond to the pyranoside ring in higher carbon sugars, a model is advanced that relates the relative configuration of the three stereogenic centers comprised of the branchpoint and of the two flanking centers (C4-C5-C6 in aldoheptoses and higher and C5-C6-C7 in sialic and ulosonic acids) to that of the simple ring-opened pentoses. Assignment of a given stereotriad as arabino, lxyo, ribo, or xylo by inspection of the Fischer projection formulas permits prediction of conformation of the exocyclic bond by comparison with the known solution (= crystal in all cases) conformations of the simple pentitols. More remote stereogenic centers in the side chain, as in the 8-position of
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