A selective α-mannosidase inhibitor
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1-Deoxymannojirimycin (hydrochloride)

Item No. 17178

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2R-(hydroxymethyl)-3R,4R,5R-piperidinetriol, monohydrochloride
CAS Number
73465-43-7
Molecular Formula
C6H13NO4 • HCl
Formula Weight
199.6
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 10 mg/mlPBS (pH 7.2): 1 mg/ml
SMILES
O[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)NC1.Cl
InChi Code
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
InChi Key
ZJIHMALTJRDNQI-MVNLRXSJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

    $31

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    5 mg

    $93

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    10 mg

    $139

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    25 mg

    $231

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    Cayman Chemical
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    Product 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.1,2 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.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Vallee, F., Karaveg, K., Herscovics, A., et al. Structural basis for catalysis and inhibition of N-glycan processing class I α1,2-mannosidases. The Journal of Biological Chemisty 275(52), 41287-41298 (2000).

    2. Bischoff, J., Liscum, L., and Kornfeld, R. The use of 1-deoxymannojirimycin to evaluate the role of various α-mannosidases in oligosaccharide processing in intact cells. The Journal of Biological Chemisty 261(10), 4766-4774 (1986).

    3. Balzarini, J. The α(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. 581(10), 2060-2064 (2007).

    4. Ogier-Denis, E., Trugnan, G., Sapin, C., et al. Dual effect of 1-deoxymannojirimycin on the mannose uptake and on the N-glycan processing of the human colon cancer cell line HT-29. The Journal of Biological Chemisty 265(10), 5366-5369 (1990).

    Product Citations

    Esposito, M., Mondal, N., Greco, T.M., et al. Bone vascular niche E-selectin induces mesenchymal-epithelial transition and Wnt activation in cancer cells to promote bone metastasis. Nat. Cell. Biol. (2019).