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: This series of molecular dynamics simulation of hevein domain (HEV32) in complex with (β-D-GlcNAc)3 shows that classical hydrogen bonds and CH/π interactions are working in concert to stabilize this carbohydrate-protein test case.
11 citations
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TL;DR: In this article, a non-aqueous solution of bromine, iodine or selenophenyl with photolytically generated stannyl radicals from appropriately substituted pyranose derivatives and their e.r.s. spectra are recorded in the temperature range from −30 to 70 °C.
Abstract: Carbohydrate free radicals are generated in non-aqueous solution by abstraction of bromine, iodine or selenophenyl with photolytically generated stannyl radicals from appropriately substituted pyranose derivatives and their e.s.r. spectra are recorded in the temperature range from –30 to 70 °C. From the hyperfine splitting parameters the preferred conformations of these sugar radicals are derived. The findings are compared with results from investigations in aqueous solution and an attempt is made to identify the factors which determine the conformations. From the α-13C coupling constant of the tetra-acetylglucosyl radical it is concluded that pyranosyl radicals are of the π-type. A novel 1,2-migration of an acetoxy group in tetra-acetylgalactosyl radical is reported. The mechanism of interaction of nitrosugars and related compounds with tin radicals is discussed.
11 citations
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TL;DR: In this paper, the pyranose ring intermediate between the boat 2,5B(D) and the twist boat 5S1(D), was verified by X-ray analysis of methyl 3,4-di-O-acetyl-2,6-anhydro-α-D-altropyranoside.
Abstract: 2,5-Dioxabicyclo[2.2.2]octane Derivatives: Conformation of Methyl 2,6-Anhydro-α-D-hexopyranosides
Ring opening of methyl 2,6:3,4-dianhydro-α-D-altropyranoside (5) with KOH in water at 150°C yields almost exclusively the hitherto unknown methyl 2,6-anhydro-α-D-mannopyranoside (6). 1H NMR spectra of this compound and of all other α-anomers of this series suggest a conformation of the pyranose ring intermediate between the boat 2,5B(D) and the twist boat 5S1(D). This was verified by X-ray analysis of methyl 3,4-di-O-acetyl-2,6-anhydro-α-D-altropyranoside (2).
11 citations
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TL;DR: Three determinants of the repeating unit of Salmonella sero-group A, B and D have been synthesized using mercury(II) iodide as a catalyst in the glycosylation reaction.
Abstract: The disaccharide 4-O-alpha-D-mannopyranosyl-alpha-L-rhamnopyranose and the trisaccharide 2-O-alpha-D-galactopyranosyl-4-O-beta-D-mannopyranosyl-alpha-L-rhamno pyranose determinants, which are analogs of the repeating unit of Salmonella sero-group A, B and D, have been synthesized using mercury(II) iodide as a catalyst in the glycosylation reaction. The reducing end of the di- and the trisaccharide was substituted with a linking arm for covalent attachment to a protein carrier. Reaction of 8-ethoxycarbonyloct-1-yl 2,3-di-O-benzoyl-alpha-L-rhamnopyranoside with acetobromomannose in the presence of mercury(II) iodide gave, after deprotection, the disaccharide in 49% yield. The trisaccharide was prepared by a block synthesis in which 6-O-acetyl-4-O-allyl-2-O-(6-O-acetyl-2-O-allyl-3,4-di-O-benzoyl-alpha-D- galactopyranosyl)-3-O-benzyl-alpha-D-mannopyranosyl bromide (21) and 8-methoxycarbonyloct-1-yl 2,3-O-cyclohexylidene-alpha-L-rhamnopyranoside were condensed in the presence of mercury(II) iodide. These conditions gave the trisaccharide (26) in 26% yield. The disaccharide 21 was prepared by mercury(II) iodide catalyzed condensation of the protected galactopyranosyl bromide (15) and 4-O-allyl-1,6-anhydro-3-O-benzyl-beta- D-mannopyranose followed by acetolysis and reaction with titanium tetrabromide.
11 citations
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TL;DR: In this paper, the authors showed that residues of d-glucose substituted with a single O-(2-hydroxypropyl) substituent at O-2 form 1,2- O -(1-methyl-1, 2-ethanediyl)-α-d -glucopyranose acetals.
11 citations