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: Molecular docking calculations of various carbohydrates into the crystal structure of P2OxA and the analysis of the protein-ligand interactions in the docked complexes enabled us to explain the substrate specificity of the enzyme by a conserved hydrogen bond pattern which is formed between the protein and all substrates.
18 citations
TL;DR: In this paper, the synthesis of D-glycero-D-altro-heptose, a constitutent of O antigen chains in lipopolysaccharides from Campylobacter jejuni serotypes O:23 and O:36, was explored.
Abstract: An exploration of the synthesis of D-glycero-D-altro-heptose, a constitutent of O antigen chains in lipopolysaccharides from Campylobacter jejuni serotypes O:23 and O:36 led to a study of the 2-tri...
18 citations
TL;DR: A second generation approach to the F ring, fragment C38-C45, of altohyrtin A (1) is described in this article, where the C43-C44 C-glycosidic linkage was prepared and subsequently functionalised with a thioketal moiety.
Abstract: A second generation approach to the F ring, fragment C38–C45, of altohyrtin A (1) is described herein. The C43–C44 C-glycosidic linkage was prepared and subsequently functionalised with a thioketal moiety.
18 citations
TL;DR: In this paper, the effect of azides on zinc-induced ring-opening reactions of deoxy halogeno sugars by dealkoxyhalogenation was investigated, and it was shown that the effect is equally effective both intra-and intermolecularly.
Abstract: Zinc/silver–graphite induced ring-opening reactions of deoxy halogeno sugars by dealkoxyhalogenation may be suppressed by bulky protecting groups in the substrates, giving rise to simple dehalogenation products. Furanose derivatives are more sensitive to such steric effects than pyranose systems, although an X-ray analysis of 1,2-O-isopropylidene-3-O-benzyl-5-deoxy-5-iodo-α-D-xylofuranose 3 shows no evidence of steric hindrance by the C-3 substituent. Moreover, dehalogenation instead of reductive ring-opening reactions are observed in all cases in which organic azides are present in the reaction medium. This unprecedented effect of azides on zinc-induced reductions is equally effective both intra-and intermolecularly. This behaviour is best rationalized by assuming radical intermediates for dehalogenations, in contrast to transient organometallic species closely bound to the zinc surface when reductive ring-opening is observed. This mechanistic interpretation is supported by a labelling experiment.
18 citations
TL;DR: In this article, new structures arising from the photolysis of peracetylated methyl 1-azido-D-glucopyranosides account for the formation of excited intermediates which undergo stereocontrolled migrations of either the O-5 oxygen atom (a) or, competitively, the O 1 oxygen atom or the C-2 carbon atom (c), depending, respectively, on the α or β orientation of the azido group in the substrate.
18 citations