Topic
Pyranose
About: Pyranose is a research topic. Over the lifetime, 1619 publications have been published within this topic receiving 35348 citations. The topic is also known as: pyranoses & hexopyranose.
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TL;DR: The active transport of methyl beta-D-Galactoside and some other analogs of D-glucose and D-galactose was studied in slices of rabbit and renal cortex and concluded that a hydroxyl at C6 is required for transport, but is not mandatory for an interaction with the carrier.
31 citations
TL;DR: It is found that a trans-fused 4O,5N-oxazolidinone group stabilizes the equatorial glycoside, i.e., reduces the anomeric effect, when compared to the4O, 5N-diacetyl protected systems.
Abstract: A method for the investigation of the influence of protecting groups on the anomeric equilibrium in the sialic acid glycosides has been developed on the basis of the equilibration of O-sialyl hydroxylamines by reversible homolytic scission of the glycosidic bond following the dictates of the Fischer–Ingold persistent radical effect. It is found that a trans-fused 4O,5N-oxazolidinone group stabilizes the equatorial glycoside, i.e., reduces the anomeric effect, when compared to the 4O,5N-diacetyl protected systems. This effect is discussed in terms of the powerful electron-withdrawing nature of the oxazolidinone system, which in turn is a function of its strong dipole moment in the mean plane of the pyranose ring system. The new equilibration method displays a small solvent effect and is most pronounced in less polar media consistent with the anomeric effect in general. The unusual (for anomeric radicals) poor kinetic selectivity of anomeric sialyl radicals is discussed in terms of the planar π-type structu...
31 citations
TL;DR: Reaction of glycosyl 2-pridyl sulfones with alcohols and samarium(III) triflate affords glycosides in moderate to excellent yields, and selectivity allowed the efficient preparation of oligosaccharides via orthogonal Glycosylation protocols.
31 citations
TL;DR: In this paper, 2-Fluoro-2-deoxy-γ-xylonic and -lyxonic lactones, 7a and 7b, were prepared via diastereoselective fluorination of the α,β-unsaturated chiral imide 5 followed by dihydroxylation.
30 citations
TL;DR: In this paper, a pool of P2O variants were generated based on rational design to change the specificity of the enzyme towards the oxidation of l-arabinose at the C2-position.
Abstract: This work reports the one-pot enzymatic cascade that completely converts l-arabinose to l-ribulose using four reactions catalyzed by pyranose 2-oxidase (P2O), xylose reductase, formate dehydrogenase, and catalase. As wild-type P2O is specific for the oxidation of six-carbon sugars, a pool of P2O variants was generated based on rational design to change the specificity of the enzyme towards the oxidation of l-arabinose at the C2-position. The variant T169G was identified as the best candidate, and this had an approximately 40-fold higher rate constant for the flavin reduction (sugar oxidation) step, as compared to the wild-type enzyme. Computational calculations using quantum mechanics/molecular mechanics (QM/MM) molecular dynamics (MD) showed that this improvement is due to a decrease in the steric effects at the axial C4-OH of l-arabinose, which allows a reduction in the distance between the C2-H and flavin N5, facilitating hydride transfer and enabling flavin reduction.
30 citations