117821-08-6

Basic information

• Product Name: (2S,3S,4S,5S)-2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol
• CAS NO: 117821-08-6
• Molecular Formula: C₇H₁₅NO₄
• Molecular Weight: 177.1983
• Mol File: 117821-08-6.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 367.2°C at 760 mmHg
• Flash Point: 220.3°C
• Density: 1.394g/cm³
• Vapor Pressure: 6.97E-07mmHg at 25°C
• Refractive Index: 1.58
• CAS DataBase Reference: (2S,3S,4S,5S)-2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,4S,5S)-2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol(117821-08-6)
• EPA Substance Registry System: (2S,3S,4S,5S)-2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol(117821-08-6)

Safety Data

• Hazardous Substances Data: 117821-08-6(Hazardous Substances Data)

Upstream product

• 50-00-0 formaldehyd 
• 19130-96-2 1,5-dideoxy-1,5-imino-D-glucitol 
• 115241-19-5 N-formyl-N-methyl-6-amino-6-deoxy-L-sorbose 
• 14199-63-4 1-deoxymannojirimycin 

Relevant articles and documents

Inhibition of intestinal α-glucosidase activity and postprandial hyperglycemia by moranoline and its N-alkyl derivatives

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5- C-Branched Deoxynojirimycin: Strategy for Designing a 1-Deoxynojirimycin-Based Pharmacological Chaperone with a Nanomolar Affinity for Pompe Disease

In recent years, the function of pharmacological chaperones as a "thermodynamic stabilizer"has been attracting attention in combination therapy. The coadministration of a pharmacological chaperone and recombinant human acid α-glucosidase (rhGAA) leads to improved stability and maturation by binding to the folded state of the rhGAA and thereby promotes enzyme delivery. This study provides the first example of a strategy to design a high-affinity ligand toward lysosomal acid α-glucosidase (GAA) focusing on alkyl branches on 1-deoxynojirimycin (DNJ); 5-C-heptyl-DNJ produced a nanomolar affinity for GAA with a Ki value of 0.0047 μM, which is 13-fold more potent than DNJ. The protein thermal shift assay revealed that 10 μM 5-C-heptyl-DNJ increased the midpoint of the protein denaturation temperature (Tm) to 73.6 °C from 58.6 °C in the absence of the ligand, significantly improving the thermal stability of rhGAA. Furthermore, 5-C-heptyl-DNJ dose dependency increased intracellular GAA activities in Pompe patient's fibroblasts with the M519V mutation. The introduction of C5 alkyl branches on DNJ provides a new molecular strategy for pharmacological chaperone therapy for Pompe disease, which may lead to the development of higher-affinity and practically useful chaperones.

Antiviral compounds

A method of inhibiting lentivirus is disclosed which comprises mammalian host susceptible to said lentivirus with a virally inhibitory effective amount of an O-acylated derivative of 1,5-dideoxy-1,5-imino-D-glucitol and their N-alkyl, N-acyl and N-aroyl derivatives in which from one to four of the free hydroxyl groups are O-acylated with carboxylic alkanoyl radicals selected from the group consisting of ω,ω,ω-trifluoroalkanoyl having from three to eight carbon atoms, carboxylic cycloalkanoyl groups having from four to eight carbon atoms and carboxylic acyclic alkanoyl groups having from two to ten carbon atoms, wherein the N-aroyl groups contain from 7 to 14 carbon atoms, the N-acyl groups contain from 4 to 8 carbon atoms and the N-alkyl groups contain from 1 to 14 carbon atoms.