A facile synthesis of a complex type N-glycan thiazoline as an effective inhibitor against the antibody-deactivating endo-β-N-acetylglucosaminidases |
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Authors: | Chao Li Shilei Zhu Xin Tong Chong Ou |
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Institution: | Department of Chemistry and Biochemistry, University of Maryland, Regents Drive, College Park, Maryland, USA |
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Abstract: | Endo-β-N-acetylglucosaminidases are a class of endoglycosidases that deglycosylate N-glycans from glycoproteins. We describe here a facile synthesis of a complex type N-glycan thiazoline as a new mechanism-based inhibitor for this class of enzymes. The synthesis started with the readily available sialoglycopeptide (SGP) and its conversion into the glycan thiazoline through several enzymatic and chemical reactions. The synthetic glycan thiazoline showed potent inhibitory activity against several endoglycosidases including the two antibody-deactivating enzymes, Endo-S and Endo-S2, from human pathogen Streptococcus pyogenes, which would be useful as tools for structural and functional studies of these enzymes. |
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Keywords: | Oligosaccharide thiazoline enzyme inhibitor complex type N-glycan endo-β-N-Acetylglucosaminidase antibody enzymatic deglycosylation |
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