73285-50-4 Usage
Description
1-Deoxynojirimycin (1-DNJ) is an iminosugar that has been found in M. alba (mulberry) leaves and has diverse biological activities. It inhibits the activities of α- and β-glucosidase (IC50s = 35 and 71 μM, respectively). 1-DNJ (5 mM) reduces the formation of N-linked complex oligosaccharides in IEC-6 cells. It inhibits HIV-1 envelope-mediated membrane fusion in CEM cells when used at a concentration of 2 mM. 1-DNJ (1-100 μg/ml) reduces the invasion and migration of B16/F10 mouse melanoma cells. It improves 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.
Chemical Properties
White Crystalline Solid
Uses
natural chitin synthase inhibitor
General Description
Specific glucosidase inhibitor, including trimming glucosidases I and II, that sequentially removes the three glucose residues from precursor Glc3Man9GlcNAc2 in N-linked glycan biosynthesis.
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.
