Infra-red Spectra of Deuterium-labelled Carbohydrates

Barker, S. A.; Moore, R. H.; Stacey, M.; Whiffen, D. H.

doi:10.1038/186307a0

Cited by 13 publications

(6 citation statements)

References 6 publications

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“…While a comparable IR absorbance for oligosaccharides is found in the OH stretching band region (i.e., 3 µm), the fingerprint region shows the most marked spectral differences between isomers. [60][61][62][63] These same differences would be anticipated in the gas phase for ionic species, with three provisos: (1) Many bands would be shifted to different fundamental frequencies due to the absence of intermolecular interaction (solvent or solid phase) effects. (2) Li + attachment could have significant effects on these frequencies.…”

Section: Resultsmentioning

confidence: 83%

Differentiation of Isomers by Wavelength-Tunable Infrared Multiple-Photon Dissociation-Mass Spectrometry: Application to Glucose-Containing Disaccharides

et al. 2005

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Variation in the wavelength of irradiation in infrared multiple-photon dissociation (IR-MPD) of lithium-tagged glucose-containing disaccharide ions (1-2-, 1-3-, 1-4-, and 1-6-linked isomers of both anomeric configurations) resulted in marked differences in their mass spectral fragmentation patterns. Two-dimensional plots of the fragment yield versus infrared wavelength for each mass spectral product ion were unique for each isomer and can be considered a spectral fingerprint. Individual product ions or diagnostic ratios of key product ions can be optimized at specific IR wavelengths. The technique permits both linkage position and anomeric configuration to be assigned. The ratio of the fragments derived by cleavage at the glycosidic bond (m/z 169/187) is much enhanced for beta-anomers compared to alpha-anomers. Differences in the diagnostic product ions 169 and 187 were largest in the range of 9.0-9.4 microm, where the maximum dissociation yield was observed. Conversely, at 10.6 microm, the wavelength of nontunable CO2 lasers that accompany commercial Fourier transform ion cyclotron resonance mass spectrometers, the dissociation yield was poor and anomeric differentiation was not possible. In contrast to previous studies by collision-induced dissociation, the trends in dissociation behavior between anomers using IR-MPD are significant and allow simple diagnostic rules to be established. By depositing energy into these isobaric ions via narrow-band IR excitation, the resulting internal energy can be finely controlled, thereby obtaining high reproducibility in dissociation patterns. Given the multidimensionality of variable-wavelength IR-MPD of lithiated disaccharides, it is expected that this approach can overcome some of the current limitations in isomer differentiation.

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Section: Resultsmentioning

confidence: 83%

Differentiation of Isomers by Wavelength-Tunable Infrared Multiple-Photon Dissociation-Mass Spectrometry: Application to Glucose-Containing Disaccharides

et al. 2005

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“…Infrared spectra of LPS (C-M) and (H-Ph) showed absorptions due to the hydroxy -OH, the hydroxy-carbon -C-OH, the glycoside bond C-O-C, and the fatty acid methylene and methyl groups -CH., and CH:,. Absorptions at 1,735 cm-', due to esters, were weak; intense absorptions at 1,630 to 1,675 cm-' due to amide bonds, -CONH-, indicated the presence ofN-acyl hexosamines as the predominant form of fatty acid linkage (5). This supposition is supportd by the relative resistance of the LPS to saponification.…”

Section: Resultsmentioning

confidence: 92%

“…The dried material was dissolved in a small volume of water and chromatographed on paper. To prepare samples for GLC, 2 to 5 mg of LPS was hydrolyzed with 0.25 N H2SO4 in vacuo in a sealed tear bulb at 100 C for 16 h. The hydrolysate was neutralized with BaCO:,, reduced with sodium borohydride, and then acetylated (5). The resultant alditol acetates were analyzed on column A with a temperature programmed from 170 to 205 C, at 2 C/min.…”

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confidence: 99%

Further characterization of a lipopolysaccharide from Coxiella burneti

Chan¹,

McChesney²,

Paretsky³

1976

Infect Immun

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The lipopolysaccharide previously isolated from the rickettsial agent of Q fever, Coxiella burneti, phase I, has been further characterized. The sugar residues ribose, mannose, glucose, D-glycero-D-mannoheptose, and L-glycero-Dmannoheptose are present. Two sugars remain unidentified, one of which is a minor and the other a major constituent. Isomyristic, palmitic, and /3-hydroxymyristic acids are the major fatty acid residues of the 15 identified. The nature and content of other lipopolysaccharide constituents are presented.Toxins have been identified in several rickettsial species, but until recently no endotoxin had been described for Coxiella burneti, the rickettsial agent of Q fever. Baca and Paretsky prepared a lipopolysaccharide (LPS) from C. burneti, phase I, which has many pharmacological properties characteristic of the endotoxins of gram-negative bacteria (3). We now describe a more extensive chemical characterization of the LPS of C. burneti.MATERIALS AND METHODS C. burneti, Nine Mile strain, phase I, was cultivated in embryonated eggs and subsequently purified from infected yolk sacs (33). The LPS was prepared by a modified hot phenol-water method (4, 36). Purified rickettsiae (2 to 4 g, wet weight) were suspended in 20 ml of 0.02 M phosphate buffer-0.15 M KCl, pH 7.4 (PK), and 20 ml of 90% redistilled phenol (wt/wt), 68 C, was immediately added. The suspension was vigorously shaken for 20 min in a water bath at 68 C. The emulsion was centrifuged at 3,000 x g for 15 min, and the aqueous phase was collected. The residual interphase and phenolic phase were extracted twice more with an equal volume of PK, and the aqueous phases were collected, pooled, and dialyzed against running tap water for 3 days. The residual opalescent solution was centrifuged at 10,000 x g for 20 min at 4 C. To the supernatant were added enough 0.5 M tris(hydroxymethyl)aminomethane buffer and 0.5 M MgCl2 to give a final concentration of 0.025 M tris(hydroxymethyl)aminomethane, pH 7.5, and 0.01 M MgCl2, together with 100 gg of ribonuclease (Sigma type

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“…For PTA-2, the broad and strong absorption peak at 3390 cm −1 corresponds to the stretching vibration peak of −OH; the absorption peak at 2920 cm −1 corresponds to the stretching vibration of saturated C−H, which is the characteristic absorption peak of a polysaccharide; the absorption peak at 1620 cm −1 is the CO asymmetric stretching vibration of carboxyl group; the obvious absorption peak at 1410 cm −1 is the variable-angle vibration of C−H; the peak at 1080 cm −1 indicated the existence of furan rings; the vibration absorption peak at 890 cm −1 indicated the presence of a β glucosidic bond. 30 The vibration absorption peak at 629 cm −1 is the characteristic absorption peak of glucose. The above analysis results showed that PTA-2 is glucopyranosyl or rhamnopyranosyl polysaccharide with β glucosidic bonds.…”

Section: Resultsmentioning

confidence: 99%

Isolation, Identification, and Anti-Inflammatory Activity of Polysaccharides of Typha angustifolia

et al. 2021

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The present study aimed to purify, structurally characterize, and evaluate the anti-inflammatory activity of the polysaccharide extracted from Typha angustifolia. Two purified polysaccharides (PTA-1 and PTA-2) were obtained via DEAE-52 cellulose chromatography. Their structural characterizations and antioxidant activity were in vitro analyzed. To evaluate the anti-inflammatory activity of PTA-2, the levels of inflammatory cytokines, intracellular ROS production, and the inhibitory effects of the transcriptional activation of the nuclear factor kappa B (NF-κB) signaling pathway were determined. PTA-1 comprises glucose (100%) with α-(1 → 3) glycosidic bonds, and PTA-2 comprises glucose (66.7%) and rhamnose (33.3%) formed by β-(1 → 3) glycosidic bonds. PTA-1 and PTA-2 showed strong antioxidant activity in vitro. Moreover, PTA-2 intervention (50, 100, and 200 μg/mL) suppressed the production of inflammatory cytokines, the activation of NF-κB signaling, and reactive oxygen species production significantly. The results identified PTA-2 as a natural product that could be applied in anti-inflammatory drugs.

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Infra-red Spectra of Deuterium-labelled Carbohydrates

Cited by 13 publications

References 6 publications

Differentiation of Isomers by Wavelength-Tunable Infrared Multiple-Photon Dissociation-Mass Spectrometry: Application to Glucose-Containing Disaccharides

Differentiation of Isomers by Wavelength-Tunable Infrared Multiple-Photon Dissociation-Mass Spectrometry: Application to Glucose-Containing Disaccharides

Further characterization of a lipopolysaccharide from Coxiella burneti

Isolation, Identification, and Anti-Inflammatory Activity of Polysaccharides of Typha angustifolia

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