Characterization of the cell surface glycolipid from Spirochaeta aurantia

Paul, Catherine J.; Lyle, Elizabeth A.; Beveridge, Terry J.; Tapping, Richard I.; Kropinski, Andrew M.; Vinogradov, Evgeny

doi:10.1007/s10719-009-9230-4

Cited by 2 publications

(1 citation statement)

References 31 publications

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“…Hydrogen bonding between sugar residues has been suggested in, for example, β‐ d ‐Glc p NAc‐(1→2)‐α‐ d ‐Man p , which is a structural element in N‐ and O‐linked glycans, in α‐ d ‐Glc p ‐(1→4)‐ d ‐Glc p , that is, maltose which is a structural element in amylopectin and in cyclodextrins, and in α‐ d ‐Man p ‐(1→2)‐α‐ d ‐Man p , which is part of oligosaccharides in N‐linked glycoproteins or O‐linked in yeast . Furthermore, β‐ d ‐Glc p NAc‐(1→2)‐β‐ d ‐Man p is also a structural element in the O‐antigen polysaccharide from Escherichia coli O126 and part of the glycan in the cell surface glycolipid from Spirochaeta aurantia and it is of interest to investigate whether the anomeric configuration at the reducing end plays an important part. Likewise, partially methylated β‐cyclodextrins have a higher solubility than their non‐O‐methylated counterparts and only one potential hydrogen‐bond directionality remains in the structural element α‐ d ‐Glc p 2Me(1→4)‐ d ‐Glc p 2Me, that is, between O2′ and HO3.…”

Section: Introductionmentioning

confidence: 99%

Inter‐residual Hydrogen Bonding in Carbohydrates Unraveled by NMR Spectroscopy and Molecular Dynamics Simulations

et al. 2019

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Carbohydrates, also known as glycans in biological systems, are omnipresent in nature where they as glycoconjugates occur as oligo‐ and polysaccharides linked to lipids and proteins. Their three‐dimensional structure is defined by two or three torsion angles at each glycosidic linkage. In addition, transglycosidic hydrogen bonding between sugar residues may be important. Herein we investigate the presence of these inter‐residue interactions by NMR spectroscopy in D2O/[D6]DMSO (70:30) or D2O and by molecular dynamics (MD) simulations with explicit water as solvent for disaccharides with structural elements α‐d‐Manp‐(1→2)‐d‐Manp, β‐d‐GlcpNAc‐(1→2)‐d‐Manp, and α‐d‐Glcp‐(1→4)‐β‐d‐Glcp, all of which have been suggested to exhibit inter‐residue hydrogen bonding. For the disaccharide β‐d‐GlcpNAc‐(1→2)‐β‐d‐Manp‐OMe, the large extent of O5′⋅⋅⋅HO3 hydrogen bonding as seen from the MD simulation is implicitly supported by the 1H NMR chemical shift and 3JHO3,H3 value of the hydroxy proton. In the case of α‐d‐Glcp‐(1→4)‐β‐d‐Glcp‐OMe, the existence of a transglycosidic hydrogen bond O2′⋅⋅⋅HO3 was proven by the presence of a cross‐peak in 1H,13C HSQC‐TOCSY experiments as a result of direct TOCSY transfer between HO3 of the reducing end residue and H2′ (detected at C2′) of the terminal residue. The occurrence of inter‐residue hydrogen bonding, albeit transient, is judged important for the stabilization of three‐dimensional structures, which may be essential in maintaining a conformational state for carbohydrate–protein interactions of glycans to take place in biologically important environments.

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Section: Introductionmentioning

confidence: 99%

Inter‐residual Hydrogen Bonding in Carbohydrates Unraveled by NMR Spectroscopy and Molecular Dynamics Simulations

et al. 2019

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Enzymatic Redox Cascade for One‐Pot Synthesis of Uridine 5′‐Diphosphate Xylose from Uridine 5′‐Diphosphate Glucose

Eixelsberger

Nidetzky

2014

Adv Synth Catal

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Synthetic ways towards uridine 5′-diphosphate (UDP)-xylose are scarce and not well established, although this compound plays an important role in the glycobiology of various organisms and cell types. We show here how UDP-glucose 6-dehydrogenase (hUGDH) and UDP-xylose synthase 1 (hUXS) from Homo sapiens can be used for the efficient production of pure UDP-α-xylose from UDP-glucose. In a mimic of the natural biosynthetic route, UDP-glucose is converted to UDP-glucuronic acid by hUGDH, followed by subsequent formation of UDP-xylose by hUXS. The nicotinamide adenine dinucleotide (NAD+) required in the hUGDH reaction is continuously regenerated in a three-step chemo-enzymatic cascade. In the first step, reduced NAD+ (NADH) is recycled by xylose reductase from Candida tenuis via reduction of 9,10-phenanthrenequinone (PQ). Radical chemical re-oxidation of this mediator in the second step reduces molecular oxygen to hydrogen peroxide (H2O2) that is cleaved by bovine liver catalase in the last step. A comprehensive analysis of the coupled chemo-enzymatic reactions revealed pronounced inhibition of hUGDH by NADH and UDP-xylose as well as an adequate oxygen supply for PQ re-oxidation as major bottlenecks of effective performance of the overall multi-step reaction system. Net oxidation of UDP-glucose to UDP-xylose by hydrogen peroxide (H2O2) could thus be achieved when using an in situ oxygen supply through periodic external feed of H2O2 during the reaction. Engineering of the interrelated reaction parameters finally enabled production of 19.5 mM (10.5 g l−1) UDP-α-xylose. After two-step chromatographic purification the compound was obtained in high purity (>98%) and good overall yield (46%). The results provide a strong case for application of multi-step redox cascades in the synthesis of nucleotide sugar products.

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Characterization of the cell surface glycolipid from Spirochaeta aurantia

Cited by 2 publications

References 31 publications

Inter‐residual Hydrogen Bonding in Carbohydrates Unraveled by NMR Spectroscopy and Molecular Dynamics Simulations

Inter‐residual Hydrogen Bonding in Carbohydrates Unraveled by NMR Spectroscopy and Molecular Dynamics Simulations

Enzymatic Redox Cascade for One‐Pot Synthesis of Uridine 5′‐Diphosphate Xylose from Uridine 5′‐Diphosphate Glucose

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