73465-43-7 Usage
Description
1-Deoxymannojirimycin hydrochloride is a specific inhibitor of class I α-1,2-mannosidase, a key enzyme involved in N-glycan processing in the endoplasmic reticulum and Golgi. It is a white crystalline solid that has been used for studies on glycoprotein processing and serves as a model for the development of anticancer and antiviral therapies.
Uses
Used in Pharmaceutical Industry:
1-Deoxymannojirimycin hydrochloride is used as a selective inhibitor of α-mannosidase for its ability to block the conversion of high-mannose oligosaccharides to complex-type oligosaccharides. This inhibition is crucial for studying the role of α-mannosidase in various biological processes and for the development of potential therapeutic agents.
Used in Research Applications:
1-Deoxymannojirimycin hydrochloride is used as a research tool for investigating the role of α-1,2-mannosidase in N-glycan processing and the targeting of misfolded proteins for translocation out of the endoplasmic reticulum and degradation by the proteasome. By generating N-linked oligosaccharides with high mannose content, this compound prevents misfolded protein degradation, providing valuable insights into protein folding and quality control mechanisms.
Used in Anticancer and Antiviral Therapy Development:
1-Deoxymannojirimycin hydrochloride is used as a starting point for the development of anticancer and antiviral therapies. Its ability to inhibit α-1,2-mannosidase activity can potentially disrupt the glycosylation process in cancer cells and viral pathogens, making them more susceptible to immune recognition and clearance.
References
1) Bischoff et al. (1986), The use of 1-deoxymannojirimycin to evaluated the role of various alpha-mannosidases in oligosaccharide processing in intact cells; J. Biol. Chem., 261 4766
2) Bischoff et al. (1984), The effect of 1-deoxymannojirimycin on rat liver alpha mannosidases.; Biochem. Biophys. Res. Commun., 125 324
3) Fuhrmann et al. (1984), Novel mannosidase inhibitor blocking conversation of high mannose to complex oligosaccharides; Nature, 307 755
4) Miyake and Nagai (2009), Inhibition of alpha-mannosidase attenuates endoplasmic reticulum stress-induced neuronal cell death; Neurotoxicology, 30 144
5) Tai et al. (2011), Production of lentiviral vectors with enhanced efficiency to target dendritic cells by attenuating mannosidase activity of mammalian? cells; J. Biol. Eng., 5? 1
6) Lee et al. (2012), Construction of stable producer cells to make high-titer lentiviral vectors for dendritic cell-based vaccination; Biotechnol. Bioeng., 109 1551
Check Digit Verification of cas no
The CAS Registry Mumber 73465-43-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,3,4,6 and 5 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 73465-43:
(7*7)+(6*3)+(5*4)+(4*6)+(3*5)+(2*4)+(1*3)=137
137 % 10 = 7
So 73465-43-7 is a valid CAS Registry Number.
73465-43-7Relevant articles and documents
Looking glass inhibitors: scalable syntheses of DNJ, DMDP, and (3R)-3-hydroxy-l-bulgecinine from d-glucuronolactone and of l-DNJ, l-DMDP, and (3S)-3-hydroxy-d-bulgecinine from l-glucuronolactone. DMDP inhibits β-glucosidases and β-galactosidases whereas l-DMDP is a potent and specific inhibitor of α-glucosidases
Best, Daniel,Wang, Chen,Weymouth-Wilson, Alexander C.,Clarkson, Robert A.,Wilson, Francis X.,Nash, Robert J.,Miyauchi, Saori,Kato, Atsushi,Fleet, George W.J.
experimental part, p. 311 - 319 (2010/05/18)
A convenient large-scale synthesis of 1-deoxynojirimyin (DNJ) from d-glucuronolactone involves introduction of azide at C-5 with retention of configuration to give 5-azido-5-deoxy-1,2-O-isopropylidene-α-d-glucofuranose as a key intermediate in an overall yield of up to 72%; the same intermediate can be transformed into DMDP [(2R,3R,4R,5R)-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol] and (3R)-3-hydroxy-l-bulgecinine [(2S,3R,4R,5R)-3,4-dihydroxy-5-hydroxymethyl-l-proline]. l-Glucuronolactone, a readily available l-sugar chiron, may similarly be used to access the enantiomers l-DNJ, l-DMDP, and (3S)-3-hydroxy-d-bulgecinine. A comparison of glycosidase inhibition by DMDP (an inhibitor of β-glucosidases and β-galactosidases) and l-DMDP (a potent and specific α-glucosidase inhibitor) with the corresponding enantiomeric hydroxybulgecinines is reported; DMDP and (3R)-3-hydroxy-l-bulgecinine show weak inhibition of glycogen phosphorylase.
