Article ; Online: Synthesis of a fluorescent probe for measuring the activity of endo-β-N-acetylglucosaminidases recognizing hybrid-type N-glycans.
Bioorganic & medicinal chemistry
2024 Volume 100, Page(s) 117612
Abstract: A fluorescence-quenching-based assay system was constructed to determine the hydrolytic activity of endo-β-N-acetylglucosaminidases (ENGases) interacting with hybrid-type N-glycans. This was achieved using a dual-labeled fluorescent probe with a ... ...
| Abstract | A fluorescence-quenching-based assay system was constructed to determine the hydrolytic activity of endo-β-N-acetylglucosaminidases (ENGases) interacting with hybrid-type N-glycans. This was achieved using a dual-labeled fluorescent probe with a nonasaccharide structure. We produced the nonasaccharide skeleton by the stepwise glycosylation of the galactose residue on a galactosyl chitobiose derivative. Next, we introduced azido and acetoxy groups into the nonasaccharide derivative in a stepwise manner, which led to stereochemistry inversion at both the C-4 and C-2 hydroxy groups on its galactose residue. The protecting groups of the resulting nonasaccharide derivative were removed, and the derivative was labeled with an N-methylanthraniloyl group to obtain a reporter dye and a 2,4-dinitrophenyl group as a quenching molecule to obtain target probe 1. The use of this probe along with a microplate reader enabled a facile evaluation of the hydrolytic activities of ENGases Endo-H, Endo-M, Endo-F3, Endo-S, and Endo-CC. Furthermore, this probe could also assist in the search for novel ENGases that are specific to hybrid-type N-glycans. |
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| MeSH term(s) | Fluorescent Dyes/chemistry ; Acetylglucosaminidase/chemistry ; Galactose ; Polysaccharides/chemistry ; Glycosylation ; Mannosyl-Glycoprotein Endo-beta-N-Acetylglucosaminidase/metabolism | |||||
| Chemical Substances | Fluorescent Dyes ; Acetylglucosaminidase (EC 3.2.1.52) ; Galactose (X2RN3Q8DNE) ; Polysaccharides ; Mannosyl-Glycoprotein Endo-beta-N-Acetylglucosaminidase (EC 3.2.1.96) | |||||
| Language | English | |||||
| Publishing date | 2024-01-27 | |||||
| Publishing country | England | |||||
| Document type | Journal Article | |||||
| ZDB-ID | 1161284-8 | |||||
| ISSN | 1464-3391 ; 0968-0896 | |||||
| ISSN (online) | 1464-3391 | |||||
| ISSN | 0968-0896 | |||||
| DOI | 10.1016/j.bmc.2024.117612 | |||||
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| Database | MEDical Literature Analysis and Retrieval System OnLINE |
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