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1-Deoxynojirimycin (hydrochloride)

Cayman Chemical Item Number 10011718

1-dNM (hydrochloride); Moranoline (hydrochloride) (CAS 73285-50-4)

1-Deoxynojirimycin (hydrochloride) (CAS 73285-50-4)

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Description

Many glycoproteins cannot be secreted or expressed without appropriate glycosylation and subsequent deglucosylation in the endoplasmic reticulum (ER), making α-glucosidase activity important to proper cell function.1 α-Glucosidases I and II remove glucose residues from N-linked oligosaccharides attached to nascent glycoproteins in the ER enabling transit to the Golgi in their properly folded form. 1-Deoxynojirimycin (hydrochloride) (1-dNM (hydrochloride)), produced by Bacillus species, is a glucose analog that potently inhibits α-glucosidase I and II. It prevents the formation of complex N-linked oligosaccharides in yeast and intact mammalian cells by inhibiting both α-glucosidase I and II with IC50 values of ~2 µM.2,3 The FDA has granted orphan drug designation to dNM (hydrochloride) for the treatment of Pompe disease, an inherited lysosomal storage disorder caused by a mutation that alters the structure and stability of α-glucosidase. 1-dNM at a concentration 0.4 mM also inhibits virus spread in HIV-infected lymphocyte cultures by interfering with α-glucosidase activity.4,5

1 Lodish, H.F., and Kong, N. Glucose removal from N-linked oligosaccharides is required for efficient maturation of certain secretory glycoproteins from the rough endoplasmic reticulum to the Golgi complex. J Cell Biol 98 1720-1729 (1984).

2 Suanier, B., Kilker, R.D., Tkacz, J.S., et al. Inhibition of N-linked complex oligosaccharide formation by 1-deoxynojirimycin, an inhibitor of processing glucosidases. J Biol Chem 257(23) 14155-14161 (1982).

3 Suh, K., Gabel, C.A., and Bergmann, J.E. Identification of a novel mechanism for the removal of glucose residues from high mannose-type oligosaccharides. J Biol Chem 267(30) 21671-21677 (1992).

4 Montefiori, D.C., Robinson, W.E., and Mitchell, W.M. Role of protein N-glycosylation in pathogenesis of human immunodeficiency virus type 1. Proc Natl Acad Sci USA 85 9248-9252 (1988).

5 Papandréou, M., Barbouche, R., Guieu, R., et al. The a-glucosidase inhibitor 1-deoxynojirimycin blocks human immunodeficiency virus envelope glycoprotein-mediated membrane fusion at the CXCR4 binding step. Mol Pharmacol 61 186-193 (2002).

Synonyms
  • 1-dNM (hydrochloride)
  • Moranoline (hydrochloride)
Formal Name 2R-​(hydroxymethyl)-​3R,​4R,​5S-​piperidinetriol,​ hydrochloride
CAS Number 73285-50-4
Molecular Formula C6H13NO4 · HCl
Formula Weight 199.6
Formulation A crystalline solid
Purity ≥95%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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OCC1NC[C@H]​(O)​C(O)​[C@@H]​1O Cl

Background Reading

Montefiori, D.C., Robinson, W.E., and Mitchell, W.M. Role of protein N-glycosylation in pathogenesis of human immunodeficiency virus type 1. Proc Natl Acad Sci USA 85 9248-9252 (1988).

Suh, K., Gabel, C.A., and Bergmann, J.E. Identification of a novel mechanism for the removal of glucose residues from high mannose-type oligosaccharides. J Biol Chem 267(30) 21671-21677 (1992).

Lodish, H.F., and Kong, N. Glucose removal from N-linked oligosaccharides is required for efficient maturation of certain secretory glycoproteins from the rough endoplasmic reticulum to the Golgi complex. J Cell Biol 98 1720-1729 (1984).

Suanier, B., Kilker, R.D., Tkacz, J.S., et al. Inhibition of N-linked complex oligosaccharide formation by 1-deoxynojirimycin, an inhibitor of processing glucosidases. J Biol Chem 257(23) 14155-14161 (1982).

Papandréou, M., Barbouche, R., Guieu, R., et al. The a-glucosidase inhibitor 1-deoxynojirimycin blocks human immunodeficiency virus envelope glycoprotein-mediated membrane fusion at the CXCR4 binding step. Mol Pharmacol 61 186-193 (2002).

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Size Price Quantity Subtotal
1 mg $23.00 $0.00
5 mg $104.00 $0.00
10 mg $184.00 $0.00
50 mg $805.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

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Pricing updated 2012-05-25. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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