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 results suggest that the dominant feature controlling the dynamics of the interaction between sugars and membrane-bound transport receptors is the position of certain functional hydroxyl groups relative to the plane of the pyranose chair (Cl or 1C), defined by carbons 2, 3, 5, and the ring oxygen.
26 citations
TL;DR: The results indicate that there is a mosaic of different types of specific receptor sites on the dendritic membrane in female Culiseta inornata, and provide evidence for a pyranose site with specific requirements for at least two adjacent equatorial hydroxyl groups on carbons C2 and C3 and an axialHydroxyl group on C1.
26 citations
TL;DR: In this paper, a reductive cyclization procedure preserving the configuration of the preexistant asymetric centers and proceedings stereoselectively (in more favorable cases stereospecifically) when creating a new asymmetric center was proposed.
26 citations
TL;DR: A new aqueous-based, one-pot strategy that involves first converting the sugar to a C-glycoside ketone, followed by conversion to ketohydrazones or oximes is described, which demonstrates the versatility of the approach to diverse glycans, including bead immobilization and lectin analysis of acarbose.
Abstract: Glycosylation often mediates important biological processes through the interaction of carbohydrates with complementary proteins. Most chemical tools for the functional analysis of glycans are highly dependent upon various linkage chemistries that involve the reducing terminus of carbohydrates. However, because of ring opening, the structural integrity of the reducing sugar ring (pyranose or furanose) is lost during these techniques, resulting in derivatized carboydrates that markedly differ from the parent molecule. This paper describes a new aqueous-based, one-pot strategy that involves first converting the sugar to a C-glycoside ketone, followed by conversion to ketohydrazones or oximes. Hence, the C-glycoside ketones are tagged with fluorescence, colored, cationic or biotin-labeled groups or immobilized onto hydrazine-functionalized beads. No activating or protecting groups are required, and the chemistry is mild enough for a wide range of carbohydrates. We demonstrate the versatility of the approach to diverse glycans, including bead immobilization and lectin analysis of acarbose, an antidiabetic drug, to dabsyl-tagged enzyme substrates to screen cellulases, and for the analysis of plant cell wall hemicellulosics.
26 citations
TL;DR: In this paper, the pyranose ring in the 2,4-diazido compound was converted to boat conformations by means of polar 1,3-diaxial interactions.
Abstract: 1.6:3,4-Dianhydro-2-O-p-tolylsulfonyl-β-D-galactopyranose (5) ergibt mit Hydrazin und anschliesender Hydrierung 2,4-Diamino-1, 6-anhydro-2,4-didesoxy-β-D-glucopyranose (8) zu 85%. Mit Natriumazid ist aus 5 1.6-Anhydro-2.4-diazido-2.4-didesoxy-β-D-glucopyranose (10) gewinnbar. Durch starke polare 1,3-diaxiale Wechselwirkung ist der Pyranosering in der 2,4-Diazido-Verbindung 10 zur 1S0-Skew-Form 20 in der Diammonium-Verbindung 9 zur1.4 B-Boot-Form 21 verdreht.
Conformational Analysis, XIII1) Conversion of 1,6-Anhydro-β-D-glucopyranose Rings to Boat Conformations by Means of Polar 1,3-Diaxial Interactions Synthesis of 2,4-Diamino-1,6-anhydro-2,4-dideoxy-β-D-glucopyranose
Treatment of 1,6:3,4-dianhydro-2-O-p-tolylsulfonyl-β-D-galactopyranose (5) with hydrazine followed by hydrogenation leads to 2, 4-diamino-1,6-anhydro-2,4-dideoxy-β-D-glucopyranose (8) with 85% yield. 1,6-Anhydro-2, 4-diazido-2, 4-dideoxy-β-D-glucopyranose (10) is obtained by reaction of 5 with sodium azide. Strong 1,3-diaxial interaction causes twisting of the pyranose ring in the 2,4-diazido compound 10 into the 1S0-Skew form 20, in the diammonium compound 9 into the 1.4B boat form 21
26 citations