Classification of Sugar Chains of Glycoproteins by Analyzing Reducing End Oligosaccharides Obtained by Partial Acid Hydrolysis

Makino, Yasushi; Kuraya, Nahoki; Omichi, Kaoru; Hase, Sumihiro

doi:10.1006/abio.1996.0250

Cited by 16 publications

(22 citation statements)

References 6 publications

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“…The chemical modification of reduction prevents covalent attachment to solid supports to explore mucin oligosaccharides binding capabilities to various biological binding partners. Hence, various approaches for nonreductive β-elimination have been proposed using both gentle alkaline conditions [16,17], hydrazinolysis [18,19], chemical capturing of the reducing end to prevent degradation of released oligosaccharides [20][21][22][23][24], and flow systems that are quickly transporting oligosaccharides to nondegrading environments after they have been released [25,26]. The generation of O-linked oligosaccharide aldoses would allow these structures to be included in glycoarrays and thus used for high throughput screening of oligosaccharide interaction partners [27][28][29][30] to generate glycobiomarkers.…”

Section: Introductionmentioning

confidence: 99%

Negative Ion CID Fragmentation of O-linked Oligosaccharide Aldoses—Charge Induced and Charge Remote Fragmentation

Doohan

Hayes

Harhen

et al. 2011

J. Am. Soc. Mass Spectrom.

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Collision induced dissociation (CID) fragmentation was compared between reducing and reduced sulfated, sialylated, and neutral O-linked oligosaccharides. It was found that fragmentation of the [M -H] -ions of aldoses with acidic residues gave unique Z-fragmentation of the reducing end GalNAc containing the acidic C-6 branch, where the entire C-3 branch was lost. This fragmentation pathway, which is not seen in the alditols, showed that the process involved charge remote fragmentation catalyzed by a reducing end acidic anomeric proton. With structures containing sialic acid on both the C-3 and C-6 branch, the [M -H] -ions were dominated by the loss of sialic acid. This fragmentation pathway was also pronounced in the [M -2H] 2-ions revealing both the C-6 Z-fragment plus its complementary C-3 C-fragment in addition to glycosidic and cross ring fragmentation. This generation of the Z/C-fragment pairs from GalNAc showed that the charges were not participating in their generation. Fragmentation of neutral aldoses showed pronounced Z-fragmentation believed to be generated by proton migration from the C-6 branch to the negatively charged GalNAc residue followed by charge remote fragmentation similar to the acidic oligosaccharides. In addition, A-type fragments generated by charge induced fragmentation of neutral oligosaccharides were observed when the charge migrated from C-1 of the GalNAc to the GlcNAc residue followed by rearrangement to accommodate the 0,2 A-fragmentation. LC-MS also showed that O-linked aldoses existed as interchangeable α/β pyranose anomers, in addition to a third isomer (25% of the total free aldose) believed to be the furanose form.

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Section: Introductionmentioning

confidence: 99%

Negative Ion CID Fragmentation of O-linked Oligosaccharide Aldoses—Charge Induced and Charge Remote Fragmentation

Doohan

Hayes

Harhen

et al. 2011

J. Am. Soc. Mass Spectrom.

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“…Sugar Chains 2,3,4,5,7,8,9,12,13,14,20,21,26,27,28,31,33,34,36,37,38,39,40,41,49, and 50 were prepared as reported (6). The structures and designations of all the sugar chains used in the study are listed in Table 1.…”

Section: Standard Pa-sugarsmentioning

confidence: 99%

“…PA-Fuc, PA-Gal, PA-GalNAc, PA-Glc, PA-GlcNAc, PA-Man, PA-Xyl, and PA-isomaltose were prepared as described previously (4). Sugar Chains 2,3,4,5,7,8,9,12,13,14,20,21,26,27,28,31,33,34,36,37,38,39,40,41,49, and 50 were prepared as reported (6).…”

Section: Standard Pa-sugarsmentioning

confidence: 99%

“…We have previously reported an analytical procedure for typing sugar chains of glycoproteins by analyzing the reducing end pyridylamino (PA) 3 mono-and disaccharides obtained by partial acid hydrolysis (4). Here, we propose a method for the analysis of oligosaccharide structures from the reducing end terminal by combining partial acid hydrolysis and a two-dimensional sugar map.…”

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confidence: 98%

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Analysis of Oligosaccharide Structures from the Reducing End Terminal by Combining Partial Acid Hydrolysis and a Two-Dimensional Sugar Map

Makino

Omichi²,

Hase³

1998

Analytical Biochemistry

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“…A two-dimensional chromatography system featuring SEC and reversed phase separation has been used to map PA-labeled oligosaccharides from glycoproteins (Kuraya & Hase, 1996; Yamamoto et al, 1989). This method has been applied to analysis of partial acid hydrolysis products of glycoprotein glycans (Makino et al, 1996). An additivity rule was applied for the correlation of two-dimensional chromatographic elution position with glycan chemical structure (Nakagawa et al, 1995).…”

Section: Lc/ms Of Gagsmentioning

confidence: 99%

On‐line separations combined with MS for analysis of glycosaminoglycans

Zaia

2008

Mass Spectrometry Reviews

116

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The glycosaminoglycan (GAG) family of polysaccharides includes the unsulfated hyaluronan and the sulfated heparin, heparan sulfate, keratan sulfate, and chondroitin/dermatan sulfate. GAGs are biosynthesized by a series of enzymes, the activities of which are controlled by complex factors. Animal cells alter their responses to different growth conditions by changing the structures of GAGs expressed on their cell surfaces and in extracellular matrices. Because this variation is a means whereby the functions of the limited number of protein gene products in animal genomes is elaborated, the phenotypic and functional assessment of GAG structures expressed spatially and temporally is an important goal in glycomics. On-line mass spectrometric separations are essential for successful determination of expression patterns for the GAG compound classes due to their inherent complexity and heterogeneity. Options include size exclusion, anion exchange, reversed phase, reversed phase ion pairing, hydrophilic interaction, and graphitized carbon chromatographic modes and capillary electrophoresis. This review summarizes the application of these approaches to on-line MS analysis of the GAG classes.

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Classification of Sugar Chains of Glycoproteins by Analyzing Reducing End Oligosaccharides Obtained by Partial Acid Hydrolysis

Cited by 16 publications

References 6 publications

Negative Ion CID Fragmentation of O-linked Oligosaccharide Aldoses—Charge Induced and Charge Remote Fragmentation

Negative Ion CID Fragmentation of O-linked Oligosaccharide Aldoses—Charge Induced and Charge Remote Fragmentation

Analysis of Oligosaccharide Structures from the Reducing End Terminal by Combining Partial Acid Hydrolysis and a Two-Dimensional Sugar Map

On‐line separations combined with MS for analysis of glycosaminoglycans

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