The crystal and molecular structure of α-glucose

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

doi:10.1107/s0365110x52001787

Cited by 103 publications

(33 citation statements)

References 3 publications

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“…The nature of these interactions is not known; however, glycan:glycan interactions involving intermolecular hydrogen bonding have been noted in simple glycan crystals, with sucrose known to have up to six intermolecular hydrogen bonds within a crystal (36), and glucose forming two hydrogen bonds in a glucose crystal (37). Chitin forms two interchain hydrogen bonds between the C=O and NH groups and/or the C6-OH of neighboring sugars (38).…”

Section: Discussionmentioning

confidence: 99%

Glycan:glycan interactions: High affinity biomolecular interactions that can mediate binding of pathogenic bacteria to host cells

Day

Tran

Semchenko

et al. 2015

Proc. Natl. Acad. Sci. U.S.A.

108

104

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Cells from all domains of life express glycan structures attached to lipids and proteins on their surface, called glycoconjugates. Cell-tocell contact mediated by glycan:glycan interactions have been considered to be low-affinity interactions that precede highaffinity protein-glycan or protein-protein interactions. In several pathogenic bacteria, truncation of surface glycans, lipooligosaccharide (LOS), or lipopolysaccharide (LPS) have been reported to significantly reduce bacterial adherence to host cells. Here, we show that the saccharide component of LOS/LPS have direct, high-affinity interactions with host glycans. Glycan microarrays reveal that LOS/LPS of four distinct bacterial pathogens bind to numerous host glycan structures. Surface plasmon resonance was used to determine the affinity of these interactions and revealed 66 high-affinity host-glycan:bacterial-glycan pairs with equilibrium dissociation constants (K D ) ranging between 100 nM and 50 μM. These glycan:glycan affinity values are similar to those reported for lectins or antibodies with glycans. Cell assays demonstrated that glycan:glycan interaction-mediated bacterial adherence could be competitively inhibited by either host cell or bacterial glycans. This is the first report to our knowledge of high affinity glycan:glycan interactions between bacterial pathogens and the host. The discovery of large numbers of glycan:glycan interactions between a diverse range of structures suggests that these interactions may be important in all biological systems.H ost surface glycosylation is ubiquitous and is targeted by pathogenic bacteria, viruses, fungi and parasites for adherence and toxin binding and by glycosidases (1). Escherichia coli type 1 fimbriae, FimH, is one of the most widely studied glycanrecognizing protein adhesins, with specificity for monomannose to oligomannose structures with the variability of the mannose structure bound leading to different tissue tropism (2). Other glycan-recognizing adhesins expressed by bacteria include the following: Pseudomonas aeruginosa lectins 1 and 2 (PA-IL and PA-IIL) that have specificity for galactose and fucose, respectively (3); Helicobacter pylori SabA, specific for sialic acid containing glycoconjugates including sialyLewis X; and BabAspecific for fucosylated glycoconjugates including Lewis B (4, 5). Although there are numerous known glycan binding adhesins, the adhesins of some bacteria that interact with host surface glycans remain unknown.Direct interactions between surface glycans (glycan:glycan interactions) have been reported in sea sponges as heterogenous glycan interactions, and in mouse embryo development and cancer where homodimers of Lewis X (LeX) or ganglioside structures play a role in cell adhesion and growth factor receptor interactions (6, 7). Outside of these reports, glycan:glycan interactions, when noted, have generally been considered to be low-affinity, weak interactions (8) that precede high-affinity protein:glycan or protein:protein interactions (1, 2, 5, 9).Interestingly, there...

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Section: Discussionmentioning

confidence: 99%

Glycan:glycan interactions: High affinity biomolecular interactions that can mediate binding of pathogenic bacteria to host cells

Day

Tran

Semchenko

et al. 2015

Proc. Natl. Acad. Sci. U.S.A.

108

104

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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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“…The axial C(1)-O(1) bond is shorter than the usual C-O bond length by about 1-5 times the probable error and may be significant. Shortening of the axial C-OH bond on the l-position was observed by McDonald (1952) in a-D-glucose, though this has been queried by Killean, Ferrier & Young (1962). It was also observed by McGeachin (1957) character, though the precision of the determination is not high enough to warrant further discussion.…”

Section: Description Of the Structurementioning

confidence: 90%

The crystal structure of dipotassium glucose-1-phosphate dihydrate

Beevers¹,

Maconochie²

1965

Acta Crystallogr

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A complete structure determination has been made of dipotassium glucose-l-phosphate dihydrate. The crystal is monoclinic, belonging to the space-group P21 and has the following cell dimensions: a=10.44, b=9.025, c=7.518 A; fl=110°24 ".The observed density of 1.85 g.cm -s agrees with that calculated for two units of Ks. C6H1105-O. POa. 2H20 per unit cell.The structure was determined primarily by vector methods, partly using the isomorphous diammonium glucose-l-phosphate dihydrate, and refined both by difference maps and by the method of least-squares. The a-configuration on carbon (1) has been confirmed, and the angles and dimensions of the esterified phosphate group found to agree generally with those of other sugar phosphates. The crystal is bound together both by electrostatic and by hydrogen bonds.

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The crystal and molecular structure of α-glucose

Cited by 103 publications

References 3 publications

Glycan:glycan interactions: High affinity biomolecular interactions that can mediate binding of pathogenic bacteria to host cells

Glycan:glycan interactions: High affinity biomolecular interactions that can mediate binding of pathogenic bacteria to host cells

The crystal and molecular structure of β-D-glucose

The crystal structure of dipotassium glucose-1-phosphate dihydrate

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