1-Deoxymannojirimycin hydrochloride

Names

[ Name ]:
1-Deoxymannojirimycin hydrochloride

[Synonym ]:
(2R,3R,4R,5R)-3,4,5-Trihydroxy-2-(hydroxymethyl)piperidinium chloride
Piperidinium, 3,4,5-trihydroxy-2-(hydroxymethyl)-, chloride, (2R,3R,4R,5R)- (1:1)
1-deoxymannojirimycin hydrochloride
(2R,3R,4R,5R)-2-(Hydroxymethyl)piperidine-3,4,5-triol hydrochloride (1:1)

Biological Activity

[Description]:

1-Deoxymannojirimycin hydrochloride is a selective class I α1,2-mannosidase inhibitor with an IC50 of 20 μM. 1-Deoxymannojirimycin hydrochloride is also a N-linked glycosylation inhibitor and inhibits HIV‐1 strains. 1-Deoxymannojirimycin hydrochloride has antiviral activity[1][2].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Influenza Virus

Signaling Pathways >> Anti-infection >> HIV

Research Areas >> Infection

[Target]

IC50: 20 μM (α1,2-mannosidase I)[1] N-linked glycosylation[2] HIV‐1[2]

[References]

[1]. F Vallee, et al. Structural Basis for Catalysis and Inhibition of N-glycan Processing Class I Alpha 1,2-mannosidases. J Biol Chem. 2000 Dec 29;275(52):41287-98.

[2]. Jan Balzarini, et al. The alpha(1,2)-mannosidase I Inhibitor 1-deoxymannojirimycin Potentiates the Antiviral Activity of Carbohydrate-Binding Agents Against Wild-Type and Mutant HIV-1 Strains Containing Glycan Deletions in gp120. FEBS Lett. 2007 May 15;581(10):2060-4.

Chemical & Physical Properties

[ Melting Point ]:
183-185ºC

[ Molecular Formula ]:
C₆H₁₄ClNO₄

[ Molecular Weight ]:
199.633

[ Exact Mass ]:
199.061142

[ PSA ]:
92.95000

[ Appearance of Characters ]:
Powder | white to off-white

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
H2O: soluble10mg/mL

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H312-H332

[ Precautionary Statements ]:
P280

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R20/21/22

[ Safety Phrases ]:
22-24/25-36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Articles

Glycosylation of native MHC class Ia molecules is required for recognition by allogeneic cytotoxic T lymphocytes.

Glycobiology 6 , 413-421, (1996)

The question whether or not target cell N-linked carbohydrate participates in cytotoxic T lymphocyte (CTL) mediated cytolysis has been in contention for well over a decade. Much of the evidence suppor...