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1-Deoxymannojirimycin hydrochloride

Product Name1-Deoxymannojirimycin hydrochloride
CAS73465-43-7
MFC6H14ClNO4
MW199.63
EINECS
MOL File73465-43-7.mol

Chemical Properties

Melting point	183-185°C
storage temp.	Inert atmosphere,Store in freezer, under -20°C
solubility	H2O: soluble10mg/mL
form	Powder
color	white to off-white
Water Solubility	Soluble in water (50 mM)
Stability	Stable for 1 year from date of purchase as supplied. Solutions in distilled water may be stored at -20°C for up to 2 months.
InChI	1S/C6H13NO4.ClH/c8-2-3-5(10)6(11)4(9)1-7-3;/h3-11H,1-2H2;1H/t3-,4-,5-,6-;/m1./s1
InChIKey	ZJIHMALTJRDNQI-MVNLRXSJSA-N
SMILES	Cl.OC[C@H]1NC[C@@H](O)[C@@H](O)[C@@H]1O
CAS DataBase Reference	73465-43-7

Safety Information

Hazard Codes	Xn,Xi
Risk Statements	20/21/22-36/37/38
Safety Statements	22-24/25-36-37/39-26
WGK Germany	3
HS Code	2941900000
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Dermal Acute Tox. 4 Inhalation Acute Tox. 4 Oral

Usage And Synthesis

Description

1-Deoxymannojirimycin is a specific inhibitor of class I α-1,2-mannosidase (IC₅₀ = 0.02 μM), a key enzyme for N-glycan processing in the endoplasmic reticulum and Golgi and for targeting misfolded proteins for translocation out of the endoplasmic reticulum and degradation by the proteasome. By inhibiting α-1,2-mannosidase activity, this compound generates N-linked oligosaccharides with high mannose content, preventing misfolded protein degradation. This compound has been used for studies on glycoprotein processing and as a model for the development of anticancer and antiviral therapies.

Chemical Properties

White Crystalline Solid

Uses

Selective inhibitor of a-mannosidase

Uses

Deoxymannojirimycin has been shown to be a potent inhibitor of the mammalian Golgi alpha- mannosidase 1 activity, blocking the conversion of high-mannose oligosaccharides to complex-type oligosaccharides. However, it does not inhibit the biosynthesis of lipid- linked oligosaccharides.

storage

+4°C

References

[1] J BISCHOFF R K L Liscum. The use of 1-deoxymannojirimycin to evaluate the role of various alpha-mannosidases in oligosaccharide processing in intact cells.[J]. The Journal of Biological Chemistry, 1986, 261 10: 4766-4774.
[2] JOYCE BISCHOFF Rosalind K. The effect of 1-deoxymannojirimycin on rat liver α-mannosidases[J]. Biochemical and biophysical research communications, 1984, 125 1: Pages 324-331. DOI:10.1016/s0006-291x(84)80371-x
[3] ULRIKE FUHRMANN. Novel mannosidase inhibitor blocking conversion of high mannose to complex oligosaccharides[J]. Nature, 1984, 307 5953: 755-758. DOI:10.1038/307755a0
[4] KUNIO MIYAKE Kaoru N. Inhibition of α-mannosidase attenuates endoplasmic reticulum stress-induced neuronal cell death[J]. Neurotoxicology, 2009, 30 1: Pages 144-150. DOI:10.1016/j.neuro.2008.10.010
[5] APRIL TAI. Production of lentiviral vectors with enhanced efficiency to target dendritic cells by attenuating mannosidase activity of mammalian cells.[J]. Journal of Biological Engineering, 2011, 5 1: 1. DOI:10.1186/1754-1611-5-1
[6] CHI-LIN LEE. Construction of stable producer cells to make high-titer lentiviral vectors for dendritic cell-based vaccination[J]. Biotechnology and Bioengineering, 2011, 109 6: 1551-1560. DOI:10.1002/bit.24413

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