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Literature DB >> 23992636

Novel cleavage of reductively aminated glycan-tags by N-bromosuccinimide to regenerate free, reducing glycans.

Xuezheng Song¹, Brian A Johns, Hong Ju, Yi Lasanajak, Chunmei Zhao, David F Smith, Richard D Cummings.

Abstract

Glycans that are fluorescently tagged by reductive amination have been useful for functional glycomic studies. However, the existing tags can introduce unwanted properties to the glycans and complicate structural and functional studies. Here, we describe a facile method using N-bromosuccinimide (NBS) to remove the tags and efficiently regenerate free reducing glycans. The regenerated free reducing glycans can be easily analyzed by routine mass spectrometry or retagged with different tags for further studies. This new method can be used to efficiently remove a variety of fluorescent tags installed by reductive amination, including 2-aminobenzoic acid and 2-aminopyridine. NBS treatment essentially transforms the commonly used 2-aminobenzoic linkage to a cleavable linkage. It can be used to cleave printed glycans from microarrays and cleave neoglycopeptides containing a 2-aminobenzoic linker.

Entities: Chemical Disease Gene Species

Mesh：

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Year: 2013 PMID： 23992636 PMCID： PMC4266466 DOI： 10.1021/cb400513k

Source DB: PubMed Journal: ACS Chem Biol ISSN： 1554-8929 Impact factor: 5.100

24 in total

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Journal: Biochim Biophys Acta Date: 2011-07-20

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Authors: S Hase; T Ikenaka; Y Matsushima
Journal: J Biochem Date: 1979-04 Impact factor: 3.387

7. Covalent display of oligosaccharide arrays in microtiter plates.

Authors: Marian C Bryan; Fabio Fazio; Hing-Ken Lee; Cheng-Yuan Huang; Aileen Chang; Michael D Best; Daniel A Calarese; Ola Blixt; James C Paulson; Dennis Burton; Ian A Wilson; Chi-Huey Wong
Journal: J Am Chem Soc Date: 2004-07-21 Impact factor: 15.419

Novel cleavage of reductively aminated glycan-tags by N-bromosuccinimide to regenerate free, reducing glycans.

1. A comprehensive procedure for preparation of partially methylated alditol acetates from glycoprotein carbohydrates.

2. Fingerprinting of glycans as their 2-aminoacridone derivatives by capillary electrophoresis and laser-induced fluorescence.

Review 3. Glycans modulate immune responses in helminth infections and allergy.

4. Analyses of oligosaccharides by tagging the reducing end with a fluorescent compound. II. Linkage point analyses.

5. Mass spectrometric O-glycan analysis after combined O-glycan release by beta-elimination and 1-phenyl-3-methyl-5-pyrazolone labeling.

6. Analyses of oligosaccharides by tagging the reducing end with a fluorescent compound. I. Application to glycoproteins.

7. Covalent display of oligosaccharide arrays in microtiter plates.

8. Tagging of sugars with a fluorescent compound, 2-aminopyridine.

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