Matrix-assisted ultraviolet laser-desorption ionization and electrospray-ionization time-of-flight mass spectrometry of sulfated neocarrabiose oligosaccharides

Fukuyama, Yuko; Ciancia, Marina; Nonami, Hiroshi; Cerezo, Alberto S.; Erra‐Balsells, Rosa; Matulewicz, Marı́a C.

doi:10.1016/s0008-6215(02)00230-6

Cited by 36 publications

(53 citation statements)

References 22 publications

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“…Extensive desulfation has also been previously reported for sulfated neocarrabiose oligosacharides with nor-harmane as matrix. 3,16 In addition, spectral analysis was consistent again with a maximum loss of (x -1) sulfate groups, where x is the number of sulfates in the analyte, suggesting that the non-ionized sulfate groups are more easily lost than the stabilized sulfate anion or that the monocharged anion with only one sulfate group is the most stable in the UV-MALDI process. 3 Figure 3.…”

Section: Introductionmentioning

confidence: 68%

“…It is noteworthy that no loss of water was previously observed in the mass spectra of the sulfated neocarrabiose oligosaccharides determined in the same conditions. 3 This asymmetrical profile suggested a mass-dependent discrimination 17 for m/z higher than 2349.6 Da. Some of the peaks also showed a minor signal at m/z + 18 Da, which could derive from the replacement of a 3,6-anhydrogalactose unit by a non-sulfated galactose in the oligosaccharide structure.…”

Section: Introductionmentioning

confidence: 97%

“…2 The repeating units of kappa-, iota-, mu-and nu-carrageenans are shown in Figure 1. In a previous publication 3 , the feasibility of matrix-assisted ultraviolet laser-desorption ionization time-of-flight mass spectrometry (UV-MALDI-TOF-MS) of carrageenans was studied. Several commercial sulfated neocarrabiose oligosaccharides were analyzed in the positive-and negative-ion modes using 2,5-dihydroxybenzoic acid and nor-harmane as matrices.…”

Section: Introductionmentioning

confidence: 99%

“…8 Structural analysis 10 of the non-gelling carrageenan (1C 3 , molar ratio galactose:3,6-anhydrogalactose:sulfate 1.00:0.37:1.14) showed that its backbone was mainly constituted by G4S→DA (kappa-diad), G4S→DA2S (iota-diad) and G4S→D2S,6S (nu-diad) with minor contribution of G4S→D6S (mu-diad) and other diads (nomenclature of Knutsen et al) 11 .…”

Section: Introductionmentioning

confidence: 99%

“…Thus, it was assumed that: a) all the 3-linked units were sulfated in the 4-position (G4S); b) the major kappa-(G4S→DA) and mu-diads (G4S→D6S) were the only observed; and c) the 4-linked reducing end-chain residues should be, according to previous reports 4-6 on the autohydrolysis reaction, the hydrated aldehyde of 3,6-anhydrogalactose (reducing end-chain DA) or galactose 6-sulfate (reducing end-chain D6S), with high prevalence of the former according to the 13 C NMR spectrum. The m/z values of the main peaks, assigned in Table 5, corresponded to [M -Na] -or to [M + nH -nNaSO 3 -Na] -. Extensive desulfation has also been previously reported for sulfated neocarrabiose oligosacharides with nor-harmane as matrix.…”

Section: Introductionmentioning

confidence: 99%

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Autohydrolysis of a partially cyclized m/u-carrageenan and structural elucidation of the oligosaccharides by chemical analysis, NMR spectroscopy and UV-MALDI mass spectrometry

Ciancia¹,

Sato²,

Nonami³

et al. 2006

Arkivoc

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Dedicated to Prof. Rosa M. de Lederkremer on occasion of her 70 th anniversaryAbstract A partially cyclized mu/nu-carrageenan from Gigartina skottsbergii was submitted to autohydrolysis and the resulting mixture of oligosaccharides was fractionated using sequential dialysis through tubings of molecular weight cutoff 12000, 3500 and 1000. In this way four fractions were separated and characterized. Structural analysis of the major fraction, obtained from the solution inside the dialysis tubing of molecular weight cutoff 12000 (D120), was carried out. A significant difference was found by 13 C NMR spectroscopy and UV-MALDI-TOF mass spectrometry: in the 13 C NMR spectrum the reducing end-chain unit was the hydrated aldehyde of 3,6-anhydrogalactose while the UV-MALDI-TOF mass spectrum showed an unimodal distribution of even and odd peaks, suggesting fragmentation of glycosidic linkages.

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Section: Introductionmentioning

confidence: 68%

Section: Introductionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Autohydrolysis of a partially cyclized m/u-carrageenan and structural elucidation of the oligosaccharides by chemical analysis, NMR spectroscopy and UV-MALDI mass spectrometry

Ciancia¹,

Sato²,

Nonami³

et al. 2006

Arkivoc

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Z‐sinapinic acid: the change of the stereochemistry of cinnamic acids as rational synthesis of a new matrix for carbohydrate MALDI‐MS analysis

2013

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Successful application of matrix-assisted laser desorption/ionization (MALDI) MS started with the introduction of efficient matrices such as cinnamic acid derivatives (i.e. 3,5-dimethoxy-4-hydroxycinnamic acid, SA; α-cyano-4-hydroxycinnamic acid). Since the empirical founding of these matrices, other commercial available cinnamic acids with different nature and location of substituents at benzene ring were attempted. Rational design and synthesis of new cinnamic acids have been recently described too. Because the presence of a rigid double bond in its molecule structure, cinnamic acids can exist as two different geometric isomers, the E-form and Z-form. Commercial available cinnamic acids currently used as matrices are the geometric isomers trans or E (E-cinnamic and trans-cinnamic acids). As a new rational design of MALDI matrices, Z-cinnamic acids were synthesized, and their properties as matrices were studied. Their performance was compared with that of the corresponding E-isomer and classical crystalline matrices (3,5-dihydroxybenzoic acid; norharmane) in the analysis of neutral/sulfated carbohydrates. Herein, we demonstrate the outstanding performance for Z-SA. Sulfated oligosaccharides were detected in negative ion mode, and the dissociation of sulfate groups was almost suppressed. Additionally, to better understand the quite different performance of each geometric isomer as matrix, the physical and morphological properties as well as the photochemical stability in solid state were studied. The influence of the E/Z photoisomerization of the matrix during MALDI was evaluated. Finally, molecular modeling (density functional theory study) of the optimized geometry and stereochemistry of E-cinnamic and Z-cinnamic acids revealed some factors governing the analyte-matrix interaction.

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Current Literature in Journal of Mass Spectrometry

2003

J. Mass Spectrom.

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In order to keep subscribers up‐to‐date with the latest developments in their field, John Wiley & Sons are providing a current awareness service in each issue of the journal. The bibliography contains newly published material in the field of mass spectrometry. Each bibliography is divided into 11 sections: 1 Books, Reviews & Symposia; 2 Instrumental Techniques & Methods; 3 Gas Phase Ion Chemistry; 4 Biology/Biochemistry: Amino Acids, Peptides & Proteins; Carbohydrates; Lipids; Nucleic Acids; 5 Pharmacology/Toxicology; 6 Natural Products; 7 Analysis of Organic Compounds; 8 Analysis of Inorganics/Organometallics; 9 Surface Analysis; 10 Environmental Analysis; 11 Elemental Analysis. Within each section, articles are listed in alphabetical order with respect to author (2 Weeks journals ‐ Search completed at 6th. Nov. 2002)

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Matrix-assisted ultraviolet laser-desorption ionization and electrospray-ionization time-of-flight mass spectrometry of sulfated neocarrabiose oligosaccharides

Cited by 36 publications

References 22 publications

Autohydrolysis of a partially cyclized m/u-carrageenan and structural elucidation of the oligosaccharides by chemical analysis, NMR spectroscopy and UV-MALDI mass spectrometry

Autohydrolysis of a partially cyclized m/u-carrageenan and structural elucidation of the oligosaccharides by chemical analysis, NMR spectroscopy and UV-MALDI mass spectrometry

Z‐sinapinic acid: the change of the stereochemistry of cinnamic acids as rational synthesis of a new matrix for carbohydrate MALDI‐MS analysis

Current Literature in Journal of Mass Spectrometry

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