Systematic synthesis and inhibitory activity of haloacetamidyl oligosaccharide derivatives toward cytoplasmic peptide:N-glycanase

  title={Systematic synthesis and inhibitory activity of haloacetamidyl oligosaccharide derivatives toward cytoplasmic peptide:N-glycanase},
  author={A. Miyazaki and Ichiro Matsuo and Shinya Hagihara and A. Kakegawa and T. Suzuki and Y. Ito},
  journal={Glycoconjugate Journal},
  • A. Miyazaki, Ichiro Matsuo, +3 authors Y. Ito
  • Published 2008
  • Medicine, Chemistry
  • Glycoconjugate Journal
  • A series of glycosyl haloacetamides were synthesized as potential inhibitors of cytoplasmic peptide:N-glycanase (PNGase), an enzyme that removes N-glycans from misfolded glycoproteins. Chloro-, bromo-, and iodoacetamidyl chitobiose and chitotetraose derivatives exhibited a significant inhibitory activity. No inhibitory activity was observed with of fluoroacetamididyl derivatives. Moreover, N-acetylglucosamine derivatives, β-chloropropionamidyl chitobiose, and chloroacetamidyl… CONTINUE READING
    8 Citations
    Evidence for an Essential Deglycosylation-Independent Activity of PNGase in Drosophila melanogaster
    • 34
    • PDF
    Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2009–2010
    • D. Harvey
    • Chemistry, Medicine
    • Mass spectrometry reviews
    • 2015
    • 52
    ERADication of EDEM1 occurs by selective autophagy and requires deglycosylation by cytoplasmic peptide N-glycanase
    • 16
    • PDF


    Site-specific Labeling of Cytoplasmic Peptide:N-Glycanase by N,N′-Diacetylchitobiose-related Compounds*
    • 25
    • PDF
    Using a small molecule inhibitor of peptide: N-glycanase to probe its role in glycoprotein turnover.
    • 103
    Fluorescently labeled inhibitor for profiling cytoplasmic peptide:N-glycanase.
    • 23
    • PDF
    A simple, sensitive in vitro assay for cytoplasmic deglycosylation by peptide: N-glycanase.
    • 20
    Cytoplasmic peptide:N‐glycanase (PNGase) in eukaryotic cells: occurrence, primary structure, and potential functions
    • T. Suzuki, Hangil Park, W. Lennarz
    • Biology, Medicine
    • FASEB journal : official publication of the Federation of American Societies for Experimental Biology
    • 2002
    • 137
    Roles of N-linked glycans in the endoplasmic reticulum.
    • 1,737
    A role for N‐glycanase in the cytosolic turnover of glycoproteins
    • 203
    Analysis of ER-associated glycoprotein degradation using synthetic glycopeptide probes.
    • 15
    High-mannose-type glycan modifications of dihydrofolate reductase using glycan-methotrexate conjugates.
    • 31