73285-50-4 Usage
Description
Deoxynojirimycin hydrochloride, also known as 1-Deoxynojirimycin (1-DNJ), is an iminosugar derived from M. alba (mulberry) leaves. It is a specific glucosidase inhibitor that targets trimming glucosidases I and II, which are involved in the sequential removal of three glucose residues from the precursor Glc3Man9GlcNAc2 in N-linked glycan biosynthesis. Deoxynojirimycin hydrochloride exhibits a variety of biological activities, including the inhibition of αand β-glucosidase, reduction of N-linked complex oligosaccharide formation, and suppression of HIV-1 envelope-mediated membrane fusion. Additionally, it has been shown to reduce the invasion and migration of certain cancer cells and improve glucose and insulin tolerance in animal models. Deoxynojirimycin hydrochloride is a white crystalline solid.
Uses
Used in Pharmaceutical Industry:
Deoxynojirimycin hydrochloride is used as a natural chitin synthase inhibitor for its ability to inhibit the activities of αand β-glucosidase, which are essential enzymes in the synthesis of chitin, a major component of fungal cell walls. This inhibition can lead to potential applications in the development of antifungal drugs.
Used in Antiviral Applications:
Deoxynojirimycin hydrochloride is used as an antiviral agent for its ability to inhibit HIV-1 envelope-mediated membrane fusion in CEM cells. By blocking this fusion process, the compound can potentially limit the spread of the virus within the host.
Used in Anticancer Applications:
Deoxynojirimycin hydrochloride is used as an anticancer agent for its ability to reduce the invasion and migration of B16/F10 mouse melanoma cells. This suggests that the compound may have potential applications in the development of treatments for certain types of cancer.
Used in Metabolic Disorders:
Deoxynojirimycin hydrochloride is used as a treatment for metabolic disorders, specifically for improving glucose and insulin tolerance in db/db mice. When administered intravenously at doses ranging from 20 to 80 mg/kg per day for four weeks, the compound has shown promising results in enhancing glucose and insulin tolerance, which could be beneficial for the treatment of diabetes and other related conditions.
Biochem/physiol Actions
Product does not compete with ATP.
Check Digit Verification of cas no
The CAS Registry Mumber 73285-50-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,3,2,8 and 5 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 73285-50:
(7*7)+(6*3)+(5*2)+(4*8)+(3*5)+(2*5)+(1*0)=134
134 % 10 = 4
So 73285-50-4 is a valid CAS Registry Number.
InChI:InChI=1/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
73285-50-4Relevant 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.
