Mass spectrometry of uronic acid derivatives

Kováčik, Vladimı́r; Bauer, Štefan; Rosík, J.; Kòváč, Pavol

doi:10.1016/s0008-6215(00)82234-x

Cited by 91 publications

(17 citation statements)

References 9 publications

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“…1 ) and 337 (abJ 1 ) for the Gro part. [14][15][16][17] HPAEC analysis on CarboPac PA-100 of the residue revealed two major peaks that could be related to Gro (t R 2. The absence of larger structures than glucosyl-glycerol indicates that the EPS180 structure does not contain two or more consecutive (a1?3) linkages, but is built-up from isomalto-oligosaccharides, interconnected by single (a1?3) linkages.…”

Section: Smith Degradationmentioning

confidence: 99%

Structural analysis of the α-d-glucan (EPS180) produced by the Lactobacillus reuteri strain 180 glucansucrase GTF180 enzyme

Leeuwen

Kralj

Geel-Schutten

et al. 2008

Carbohydrate Research

155

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Abstract-The neutral exopolysaccharide EPS180 produced from sucrose by the glucansucrase GTF180 enzyme from Lactobacillus reuteri 180 was found to be a (1?3, 1?6)-a-D D-glucan, with no repeating units present. Based on linkage analysis, periodate oxidation, and 1D/2D 1 H and 13 C NMR spectroscopy of the intact EPS180, as well as MS and NMR analysis of oligosaccharides obtained by partial acid hydrolysis of EPS180, a composite model, that includes all identified structural features, was formulated as follows: Ó

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Section: Smith Degradationmentioning

confidence: 99%

Structural analysis of the α-d-glucan (EPS180) produced by the Lactobacillus reuteri strain 180 glucansucrase GTF180 enzyme

Leeuwen

Kralj

Geel-Schutten

et al. 2008

Carbohydrate Research

155

View full text Add to dashboard Cite

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“…J. Chem. Downloaded from www.nrcresearchpress.com by 34 plings, JI,, (0.5 HZ) and J2., (2.8 Hz). However, mannose was not detected in the polysaccharide acid hydrolysis products, which suggested this residue to be the 0-(1-carboxyethy1)-substituted hexose.…”

Section: Glycosyl Linkage Analysismentioning

confidence: 99%

“…The disaccharide 3 was conlposed of glucuronic acid and galactose. Methylation of the reduced 3 and subsequent GLC-EI-MS analysis showed diagnostic ions at nz/z 233 (aA,), 201 (aA,), and 169 (aA,), indicative of a hexopyranosyl uronate end group (34). Abundant fragment ions at'296 ( J , ) , 236 (bA,), and 204 (bA,) confirm the presence of a terminal hexitol, allowing 3 to be identified as ADsol~~rc~ c~or~fi'grrr-ariorz oj'rlzc~ cc~r-0o,ryc~rlz~~liclc~11e nrlcl car0osyerIzyl s~rl~srircier~rs Pyruvic acid acetals bridging the 0 -2 and 0 -3 positions of D-glucuronic acid residues are known as components of a number of Kle0.siella polysaccharides, but the chiralities of these components has not been reported (35).…”

Section: Glycosyl Linkage Analysismentioning

confidence: 99%

The acidic specific capsular polysaccharide of Rhodococcusequi serotype 3. Structural elucidation and stereochemical analysis of the lactate ether and pyruvate acetal substituents

Severn¹,

Richards²

1992

Can. J. Chem.

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. Can. J . Chem. 70, 2664 (1992). The specific capsular polysaccharide produced by Rhodococcus equi serotype 3 was found to be a high-molecularweight acidic polymer composed of D-glucose, D-galactose, D-glucuronic acid, 4-0-[(S)-1-carboxyethyll-D-mannose, and pyruvic acid in equal molar proportions. Structural analysis, employing a combination of chemical and nuclear magnetic resonance techniques, established that the polysaccharide is composed of linear repeating tetrasaccharide units, in which (R)-1-carboxyethylidene groups bridge the 0 -2 and 0 -3 positions of the P-D-glucuronic acid residues. The 'H and "C NMR resonances of the native and depyruvulated serotype 3 polysaccharides were fully assigned by homo-and heteronuclear chemical shift correlation methods. The absolute configurations of the lactate-substituted mannopyranosyl residues and the pyruvate acetals were determined from 'H-'H NOE measurements on the intact polysaccharide. Unequivocal determination of the absolute chirality of the 4-0-[(S)-1-carboxyethyll-P-D-mannopyranose residues was achieved by 'H-'H NOE measurements on an acetylated lactone derivative of the glycose. [Traduit par la redaction]

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“…4 Disregarding these phenomena may lead to ambiguous interpretation of the mass spectra. Therefore, the model 13 was included in the list of the compounds investigated as representative of 4,5-olefinic compounds.…”

Section: Introductionmentioning

confidence: 99%

Electrospray ionization ion‐trap multistage mass spectrometric study of sodium cationized aldobiuronic and pseudoaldobiuronic acid derivatives

et al. 2004

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Fragmentation mechanisms of electrospray ionization (ESI) mass spectrometry of aldobiuronic and pseudoaldobiuronic acid derivatives were elucidated by multistage mass spectrometric (MS(n), n = 2-5) measurements of selected ions. Characteristic under the conditions of ESI-MS analysis is the production of alkali metal (Na and K) cationized adducts. The probability the of locations of Na cations in per-O-methylated compounds was proved by quantum chemical calculations, using the Jaguar program. The most probably position of alkali metal attachment is the carboxy group of the methoxycarbonyl C-5 group of the uronic acid unit. Characteristic cleavages vary according the kind of O-derivatization. In most cases they take place on the acidic part of the dimer and at the interglycosidic oxygen atom. As a result, the criteria for the differentiation of aldobiouronic and pseudoaldobiouronic acids derivatives were elucidated.

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Mass spectrometry of uronic acid derivatives

Cited by 91 publications

References 9 publications

Structural analysis of the α-d-glucan (EPS180) produced by the Lactobacillus reuteri strain 180 glucansucrase GTF180 enzyme

Structural analysis of the α-d-glucan (EPS180) produced by the Lactobacillus reuteri strain 180 glucansucrase GTF180 enzyme

The acidic specific capsular polysaccharide of Rhodococcusequi serotype 3. Structural elucidation and stereochemical analysis of the lactate ether and pyruvate acetal substituents

Electrospray ionization ion‐trap multistage mass spectrometric study of sodium cationized aldobiuronic and pseudoaldobiuronic acid derivatives

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