CAS 108147-54-2

1-Deoxygalactonojirimycin

Description:

1-Deoxygalactonojirimycin (CAS 108147-54-2) is a carbohydrate-derived compound that belongs to the class of iminosugars. It is characterized by its ability to inhibit specific glycosidases, particularly those involved in the metabolism of carbohydrates. This inhibition can have significant implications in various biological processes, including the modulation of glycoprotein synthesis and potential therapeutic applications in treating diseases such as diabetes and certain viral infections. The compound is typically a white to off-white solid and is soluble in water, which facilitates its biological activity. Its structure features a pyrrolidine ring, which is crucial for its interaction with glycosidases. Additionally, 1-deoxygalactonojirimycin has been studied for its potential role in the treatment of lysosomal storage disorders and as an antiviral agent. Overall, its unique properties and biological activities make it a subject of interest in medicinal chemistry and pharmacology.

Formula: C₆H₁₃NO₄

InChI: InChI=1S/C6H13NO4/c8-2-3-5(10)6(11)4(9)1-7-3/h3-11H,1-2H2/t3-,4+,5+,6-/m1/s1

InChI key: InChIKey=LXBIFEVIBLOUGU-DPYQTVNSSA-N

SMILES: C(O)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)CN1

Synonyms:

• (2R,3S,4R,5S)-2-(Hydroxymethyl)-3,4,5-piperidinetriol
• 1,5-Dideoxy-1,5-imino-<span class="text-smallcaps">D</span>-galactitol
• 1-Deoxygalactonojirimycin
• 1-Deoxygalactostatin
• 3,4,5-Piperidinetriol, 2-(hydroxymethyl)-, [2R-(2α,3α,4α,5β)]-
• 3,4,5-piperidinetriol, 2-(hydroxymethyl)-, (2R,3S,4R,5S)-
• Amigal
• Migalastat
• 1,5-Dideoxy-1,5-imino-D-galactitol

1-Deoxygalactonojirimycin

CAS: 108147-54-2

Specific and potent inhibitor of lysosomal α-galactosidase with IC50 in nanomolar range. It acts as pharmacological chaperone and assists folding of the wild type and mutant versions of the enzyme. It places itself in the instable active site and prevents the damage to the enzyme during the passage through Golgi apparatus, endoplasmatic reticulum and lysosome axis. The exposure to this compound leads to increased levels of functional α-galactosidase in models for lysosomal storage disorders and brings therapeutic benefits to patients with Fabry disease.

Formula: C₆H₁₃NO₄

Purity: Min. 95%

Molecular weight: 163.17 g/mol

Ref: 3D-MD32148

Migalastat

CAS: 108147-54-2

Migalastat (GR181413A free base) is an orally administered, competitive inhibitor of α-galactosidase A (α-Gal A), demonstrating an IC50 value of 0.04 μM against

Formula: C₆H₁₃NO₄

Color and Shape: Solid

Molecular weight: 163.17

Ref: TM-T71481