73465-43-7 Usage
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
Different sources of media describe the Uses of 73465-43-7 differently. You can refer to the following data:
1. 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.
2. Selective inhibitor of a-mannosidase
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.
