1400906-90-2Relevant academic research and scientific papers
Study on metal-induced reactions of α-diazocarbonyl glucosides
Guan, Zhu,Zhang, Li-He,Sina?, Pierre,Zhang, Yongmin
, p. 8888 - 8895 (2012)
Conversions of diazocarbonyl carbohydrate compounds catalyzed by a series of rhodium and copper catalysts in conventional heating or microwave conditions were investigated. C-H insertion product was obtained in the presence of Rh 2(OAc)4. Intermolecular reactions rather than intramolecular reactions occurred in the presence of copper catalysts.
Reducing the Toxicity of Designer Aminoglycosides as Nonsense Mutation Readthrough Agents for Therapeutic Targets
Alford, Benjamin,Baradaran-Heravi, Alireza,Cameron, Scott A.,Clinch, Keith,Gan, Zhonghong,Liu, Hui,Mason, Jennifer M.,Popadynec, Michael,Powell, David A.,Rebollo, Oscar,Rendle, Phillip M.,Roberge, Michel,Whitfield, Dennis M.,Yan, Fengyang,Zubkova, Olga V.
, p. 1486 - 1492 (2021)
A significant proportion of genetic disease cases arise from truncation of proteins caused by premature termination codons. In eukaryotic cells some aminoglycosides cause readthrough of premature termination codons during protein translation. Inducing rea
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 - glycero- d - gluco-Heptopyranosyl Donor
Upadhyaya, Kapil,Bagul, Rahul S.,Crich, David
, p. 12199 - 12225 (2021)
The preparation of four per-O-benzyl-d- or l-glycero-d-galacto and d- or l-glycero-d-gluco heptopyranosyl sulfoxides and the influence of their side-chain conformations on reactivity and stereoselectivity in glycosylation reactions are described. The side-chain conformation in these donors is determined by the relative configuration of its point of attachment to the pyranoside ring and the two flanking centers in agreement with a recent model. In the d- and l-glycero-d-galacto glycosyl donors, the d-glycero-d-galacto isomer with the more electron-withdrawing trans,gauche conformation of its side chain was the more equatorially selective isomer. In the d- and l-glycero-d-gluco glycosyl donors, the l-glycero-d-gluco isomer with the least disarming gauche,gauche side-chain conformation was the most equatorially selective donor. Variable temperature NMR studies, while supporting the formation of intermediate glycosyl triflates at -80 °C in all cases, were inconclusive owing to a change in the decomposition mechanism with the change in configuration. It is suggested that the equatorial selectivity of the l-glycero-d-gluco isomer arises from H-bonding between the glycosyl acceptor and O6 of the donor, which is poised to deliver the acceptor antiperiplanar to the glycosyl triflate, resulting in a high degree of SN2 character in the displacement reaction.
