Synthesis and Biological Characterisation of Novel N‐Alkyl‐Deoxynojirimycin α‐Glucosidase Inhibitors

Illuminating glucosidases: The shown photoaffinity probe for endoplasmic reticulum (ER) α‐glucosidases was found to be a highly potent inhibitor of α‐glucosidase I in vitro and equally effective at inhibiting cellular ER glucosidases, as determined by a free oligosaccharide (FOS) analysis.

[1]  R. Dwek,et al.  Glucosylated free oligosaccharides are biomarkers of endoplasmic- reticulum alpha-glucosidase inhibition. , 2008, The Biochemical journal.

[2]  Joel L Sussman,et al.  Crystal structures of complexes of N-butyl- and N-nonyl-deoxynojirimycin bound to acid beta-glucosidase: insights into the mechanism of chemical chaperone action in Gaucher disease. , 2007, The Journal of biological chemistry.

[3]  T. Butters.  Pharmacotherapeutic strategies using small molecules for the treatment of glycolipid lysosomal storage disorders , 2007, Expert opinion on pharmacotherapy.

[4]  P. Compain,et al.  Alpha-1-C-octyl-1-deoxynojirimycin as a pharmacological chaperone for Gaucher disease. , 2006, Bioorganic & medicinal chemistry.

[5]  M. Wilke,et al.  Rescue of functional delF508‐CFTR channels in cystic fibrosis epithelial cells by the α‐glucosidase inhibitor miglustat , 2006, FEBS letters.

[6]  J. Sancho,et al.  Miglustat (NB-DNJ) works as a chaperone for mutated acid beta-glucosidase in cells transfected with several Gaucher disease mutations. , 2005, Blood cells, molecules & diseases.

[7]  D. Burton,et al.  Glycosylation: disease targets and therapy. , 2005, Advances in experimental medicine and biology.

[8]  R. Dwek,et al.  Cellular effects of deoxynojirimycin analogues: inhibition of N-linked oligosaccharide processing and generation of free glucosylated oligosaccharides. , 2004, The Biochemical journal.

[9]  R. Dwek,et al.  Cellular effects of deoxynojirimycin analogues: uptake, retention and inhibition of glycosphingolipid biosynthesis. , 2004, The Biochemical journal.

[10]  R. Spiro.  Role of N-linked polymannose oligosaccharides in targeting glycoproteins for endoplasmic reticulum-associated degradation , 2004, Cellular and Molecular Life Sciences CMLS.

[11]  Jie Feng,et al.  Synthesis of a novel photoaffinity derivative of 1-deoxynojirimycin for active site-directed labeling of glucosidase I. , 2004, Glycobiology.

[12]  L. Pickering,et al.  Preparation, biochemical characterization and biological properties of radiolabelled N-alkylated deoxynojirimycins. , 2002, The Biochemical journal.

[13]  Raymond A. Dwek,et al.  Targeting glycosylation as a therapeutic approach , 2002, Nature Reviews Drug Discovery.

[14]  R. Dwek,et al.  Molecular requirements of imino sugars for the selective control of N-linked glycosylation and glycosphingolipid biosynthesis , 2000 .

[15]  T. Butters,et al.  Synthesis of α‐Glucosidase I Inhibitors Showing Antiviral (HIV‐1) and Immunosuppressive Activity , 1996 .

[16]  H. Ploegh,et al.  Chemical modification of the glucosidase inhibitor 1-deoxynojirimycin. Structure-activity relationships. , 1991, The Journal of biological chemistry.

[17]  G. Fleet,et al.  The antibody binding site. Labelling of a specific antibody against the photo-precursor of an aryl nitrene. , 1972, The Biochemical journal.

[18]  J. Knowles,et al.  Affinity Labelling of Antibodies with Aryl Nitrene as Reactive Group , 1969, Nature.