Nonselective and Efficient Fluorescent Labeling of Glycans Using 2-Amino Benzamide and Anthranilic Acid

Bigge, J C; Patel, T.P.; Bruce, Jim; Goulding, Paul N.; Charles, Shakira; Parekh, Raj B.

doi:10.1006/abio.1995.1468

Cited by 805 publications

(555 citation statements)

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“…Fluorescent Labeling of the Oligosaccharide-reducing Terminus with 2-aminobenzamide (2AB)-2AB labeling was carried out using the Oxford GlycoSystems Signal labeling kit (30).…”

Section: Methodsmentioning

confidence: 99%

The Glycosylation of the Complement Regulatory Protein, Human Erythrocyte CD59

Rudd

Morgan

Wormald

et al. 1997

Journal of Biological Chemistry

164

104

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“…Fluorescent Labeling of the Oligosaccharide-reducing Terminus with 2-aminobenzamide (2AB)-2AB labeling was carried out using the Oxford GlycoSystems Signal labeling kit (30).…”

Section: Methodsmentioning

confidence: 99%

The Glycosylation of the Complement Regulatory Protein, Human Erythrocyte CD59

Rudd

Morgan

Wormald

et al. 1997

Journal of Biological Chemistry

164

104

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“…During the first step a Schiff-base is formed in the presence of an acid catalyst, followed by reduction to form a stable conjugate in the second step. For this latter, sodiumcyanoborohydride (NaBH 3 CN) is used in most instances as reductive agent [22], but other methods utilizing sodium-triacetoxyborohydride (NaBH(O 2 CCH 3 ) 3 ) [23], borane-diethylamine ((CH 3 ) 2 NHBH 3 ) [24], 2-picoline-borane (pic-BH 3 ) [25] or by the recently introduced transfer hydrogenation technique [26] have also been reported. The reaction speed and yield of this acidcatalyzed labeling reaction is greatly influenced by the amount and type of acid used.…”

Section: Introductionmentioning

confidence: 99%

Evaporative fluorophore labeling of carbohydrates via reductive amination

Reider

Szigeti

Guttman

2018

Talanta

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As analytical glycomics became to prominence, newer and more efficient sample preparation methods are being developed. Albeit, numerous reductive amination based carbohydrate labeling protocols have been reported in the literature, the preferred way to conduct the reaction is in closed vials. Here we report on a novel evaporative labeling protocol with the great advantage of continuously concentrating the reagents during the tagging reaction, therefore accommodating to reach the optimal reagent concentrations for a wide range of glycan structures in a complex mixture. The optimized conditions of the evaporative labeling process minimized sialylation loss, otherwise representing a major issue in reductive amination based carbohydrate tagging. In addition, complete and uniform dispersion of dry samples was obtained by supplementing the low volume labeling mixtures (several microliters) with the addition of extra solvent (e.g., THF).Evaporative labeling is an automation-friendly glycan labeling method, suitable for standard open 96 well plate format operation. Graphical abstract 2/13

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“…Incorporation of an aromatic amine allows for the facile detection of carbohydrates that generally lack strong UV absorbance, secondly it provides a reactive group necessary to introduce the tag to the reducing end of glycans using well established reductive amination protocols, 28 where each carbohydrate will be labeled under mild conditions that have been shown to produce high reductive amination yields with minimal side reactions. 28 An increase in the hydrophobicity was also desirable as this has been shown to increase the ability of carbohydrates to ionize. 29 The incorporation of charged moieties to the tag was considered undesirable as it would be expected to alter the glycan product ion patterns and may be more likely to undergo partial or complete loss of the tag.…”

Section: Introductionmentioning

confidence: 99%

Tags for the Stable Isotopic Labeling of Carbohydrates and Quantitative Analysis by Mass Spectrometry

2007

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Although stable isotopic labeling has found widespread use in the proteomics field, its application to carbohydrate quantification has been limited. Herein we report the design, synthesis, and application of a novel series of compounds that allow for the incorporation of isotopic variation within glycan structures. The novel feature of the compounds is the ability to incorporate the isotopes in a controlled manner, allowing for the generation of four tags that vary only in their isotopic content. This allows for the direct comparisons of three samples or triplicate measurements with an internal standard within one mass spectral analysis. Quantitation of partially depolymerized glycosaminoglycan mixtures, as well as N-linked glycans released from fetuin, is used to demonstrate the utility of the tetraplex tagging strategy.

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Nonselective and Efficient Fluorescent Labeling of Glycans Using 2-Amino Benzamide and Anthranilic Acid

Cited by 805 publications

References 0 publications

The Glycosylation of the Complement Regulatory Protein, Human Erythrocyte CD59

The Glycosylation of the Complement Regulatory Protein, Human Erythrocyte CD59

Evaporative fluorophore labeling of carbohydrates via reductive amination

Tags for the Stable Isotopic Labeling of Carbohydrates and Quantitative Analysis by Mass Spectrometry

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