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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)

See more	Inhibitors (493) Carbohydrate Research (10) Infectious Disease (64)

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	Copy SMILES to clipboard 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

Pricing updated 2012-02-12. Prices are subject to change without notice.

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