The crystal structure of α-<scp>D</scp>-glucose

McDonald, T. R. R.; Beevers, C. A.

doi:10.1107/s0365110x50001087

Cited by 38 publications

(15 citation statements)

References 3 publications

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“…The author has undertaken a detailed examination of the crystal structure of E-D-glucose as a preliminary to a study of other more complex cellulose oligosaccharides. McDonald & Beevers (1950, 1952 determined the crystal structure of a-D-glucose and more recently Killean, Ferrier & Young (1962) determined the structure of a-D-glucose monohydrate. Both structures showed that the pyranose ring possessed the Sachse trans configuration.…”

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confidence: 99%

The crystal and molecular structure of β-D-glucose

Ferrier¹

1963

Acta Cryst

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fl-D-Glucose (C6HlzO6) consists of a pyranose ring with substituents which are all equatorial. It crystallizes in the orthorhombic system with a = 9.29 ___ 0.04, b = 12-65 _ 0.02, c = 6.70 ___ 0.02 A. The space group is P212121 with 4 molecules in the cell. The crystal structure has been solved by a combination of a direct method and trial and error applied to two-dimensional data. The final refinement was obtained by an anisotropic least-squares analysis of approximately 850 observed three-dimensional structure factors. The three positional and six thermal parameters of all atoms except hydrogens have been determined.The pyranose ring is in the Sachse trans configuration and the ring oxygen bond angle is determined as 113 °. The detailed stereochemistry is compared with that of a-D-glucose and cellobiose.

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confidence: 99%

The crystal and molecular structure of β-D-glucose

Ferrier¹

1963

Acta Cryst

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“…However, the fructofuranosyl portion of crystalline sucrose (7) and the ribofuranosyl moiety of crystalline cytidine ( 8 ) were both found to have non-planar ring structures. 1Iore recently specific conformations, based up011 nuclear magnetic resonance spectroscopy, have been proposed for D-ribofuranose in purine and pyrimidine nucleosides (9), in thymidine (lo), in certain deoxyribonucleosides (11) and nucleotides (12), and in 1,3,5-tri-0-benzoyl-a-D-ribofuranose, rnethyl2,3-anhydroa-D-ribofuranoside, and its 0-anomer (13).…”

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confidence: 99%

Glycosidation of Sugars: Ii. Methanolysis of D-Xylose, D-Arabinose, D-Lyxose, and D-Ribose

Bishop¹,

Cooper²

1963

Can. J. Chem.

117

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Rates of methanolysis reactions of D-xylose, D-arabinose, D-Iyxose, and D-ribose have been determined. I t was found that nletha~lolysis of a pentose proceeds to equilibrium through four distiilguishable, competing reactions: (1) pentose 4 furanosides; ( 2 ) a~lomerizatioll of furanosides; (3) furanosides + pyranosides; (4) anomerizatio~l of pyranosides. The glycoside compositions a t equilibrium are interpreted in terms of stabilities of each of the four glycosides from each sugar as influenced by steric and ionic effects; a system of conformational analysis of furanoside rings is presented. The free energies of reaction in anomerization of pyranosides were in excellent agreement with values calculated from prel-iously reported interaction energies in the pyranoid ring. The relative rates of the reactions were consistent with the view that non-bonded interactions in the methyl glycosides are relieved in the transition states for their interconversions.The first paper (1) in this series described a study of the reactions of D-xylose in methanolic hydrogen chloride; the four methyl D-xylosides, products of the reaction, were analyzed a t different times by gas-liquid chroinatography of their fully methylated derivatives. The resulting rate data showed that four reactions could be distinguished:(I) xylose 4 methyl furanosides, (2) anomerization of furanosides, (3) furanosides + pyranosides, (4) anomerization of pyranosides; a tentative mechanism was proposed.The present paper describes an extension of this work to the other pentoses, D-arabinose, D-lyxose, and D-ribose; some of the reactions in the D-xylose series were repeated to obtain comparable data. I t is shown that the lnethanolysis of each pentose proceeds via the reactions given above. The equilibrium compositions can be interpreted in terms of relative stabilities of each of the four glycosides from each sugar and the relative reaction rates indicated that non-bonded interactions in the methyl glycosides are relieved in the transition states for their interconversions.The conditions cited for the reactions were-carefully controlled and products in the D-xylose and D-arabinose series were analyzed by gas-liquid chromatography of their fully methylated derivatives as described previously (1). Reaction products'in the D-lyxose and D-ribose series were analyzed by gas-liquid chromatography of their fully acetylated derivatives because of the better separations obtained. The rate a t which reducing sugar disappeared was measured by gas-liquid chromatography of the acetylated reaction mixture; the pentopyranose tetraacetates, arising from the reducing sugars, were widely separated from the methyl tri-0-acetyl pentosides. Separation of individual methyl tri-0-acetyl pentosides in this procedure, although not always complete, was sufficient t o provide information about the early products of reaction. The use of acetylation avoided the correction required (I) when the methylation procedure was used on reaction mixtures in which reducing sugars were present. The ...

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“…Figure 1 shows the X‐ray diffraction patterns of a physical mixture of crystalline G α (60%) and crystalline G β (40%) recorded before and just after a 14 h comilling process at −15°C. Before milling, the X‐ray diffraction pattern appears to be the superimposition of the X‐ray diffraction patterns of the crystalline forms of pure G α and pure G β which have the same space group P 2 1 2 1 2 1 9, 10. After comilling, all Bragg peaks have totally disappeared so that the X‐ray diffraction pattern appears to be similar to that of the quenched liquid also shown in Figure 1 for comparison.…”

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confidence: 82%