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 outcome of these experiments demonstrated that 2 –desoxysugars give a much more intense color with Schiff's reagent than their normal analogues do under comparable conditions, an effect enhanced if they are prevented from existing in the pyranose form.
Abstract: Publisher Summary This chapter presents the chemistry of the 2-desoxysugars. The 2-desoxypentoses form the carbohydrate component of the desoxynucleic acids, and are therefore of particular biological importance. The outcome of these experiments demonstrated that 2 –desoxysugars give a much more intense color with Schiff's reagent than their normal analogues do under comparable conditions, an effect enhanced if they are prevented from existing in the pyranose form. The best-known and probably still the most direct method for the synthesis of 2-desoxysugars is the Fischer glycal method. 2-desoxysugars may also be obtained by the addition of hydrogen bromide to glycals. The replacement of toluene- p -sulfonyloxy and methane-sulfonyloxy groups by iodine, using sodium iodide in acetone, has not been of great value in synthesizing 2-desoxysugars. 2-Desoxysugars are characterized by their ease of conversion to 0-glycosides. An outstanding property of the 0-glycosides of 2-desoxysugars is their lability towards acids, a property still further enhanced in the 2,3-didesoxysugar series.
16 citations
TL;DR: Investigating the tandem mass spectrometry of regiospecifically labeled, deprotonated sucrose analytes utilizes density functional theory calculations to model the pertinent gas-phase fragmentation chemistry of the prevalent glycosidic bond cleavages and compares these predictions to infrared spectroscopy experiments on the resulting B1 and C1 product anions.
16 citations
TL;DR: Four differently N-protected 3,4,6-tri-O-acetyl-2-amino- 2-deoxy-d-glucopyranosyl chlorides were synthesized and used as glycosyl donors in reactions with diosgenin and Structural evidence is presented for a mesomeric effect in both groups.
16 citations
TL;DR: To improve some of the catalytic properties of P2Ox from Trametes multicolor, saturation mutagenesis of the amino acid His450 located at a pivotal point of the active site loop and subsequent screening of the libraries thus obtained for improved activity with the sugar substrate d-galactose is selected.
Abstract: The homotetrameric flavoprotein pyranose 2-oxidase (P2Ox) has several proposed biotechnological applications, among others as a biocatalyst for carbohydrate transformations toward higher-value products. To improve some of the catalytic properties of P2Ox from Trametes multicolor, we selected a semirational enzyme engineering approach, namely, saturation mutagenesis of the amino acid His450 located at a pivotal point of the active site loop and subsequent screening of the libraries thus obtained for improved activity with the sugar substrate d-galactose. A variant with improved catalytic characteristics identified was H450G, which showed a significant, 3.6-fold decrease in KM together with a 1.4-fold increase in kcat for its substrate d-galactose and an overall improvement in the catalytic efficiency by a factor of 5. By combining H450G with other amino acid replacements, we obtained the P2Ox variants H450G/V546C and H450G/E542K/V546C, which can be of interest for applications in food industry due to their...
15 citations
TL;DR: In this article, a trifluoromethanesulfonate-catalyzed solvent-free per-O-acetylation with stoichiometric acetic anhydride proceeds in high yield to afford exclusively pyranose products as anomeric mixtures.
15 citations