AMP-Deoxynojirimycin

• CAT Number: R036547
• CAS Number: 216758-20-2
• Molecular Formula: C22H39NO5
• Molecular Weight: 397.556
• Purity: ≥95%
• Synonyms: Adamantane-pentyl-dNM;AMP-dNM;N-(5-adamantane-1-yl-methoxy-pentyl)-Deoxynojirimycin
• Storage: -20°C
• IUPAC Name: (2R,3R,4R,5S)-1-[5-(1-adamantylmethoxy)pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
• InChI: InChI=1S/C22H39NO5/c24-13-18-20(26)21(27)19(25)12-23(18)4-2-1-3-5-28-14-22-9-15-6-16(10-22)8-17(7-15)11-22/h15-21,24-27H,1-14H2/t15?,16?,17?,18-,19+,20-,21-,22?/m1/s1
• InChIKey: XVYLNHVEAOOEGI-FAIWKWDXSA-N
• SMILES: C1C2CC3CC1CC(C2)(C3)COCCCCCN4CC(C(C(C4CO)O)O)O

AMP-Deoxynojirimycin (CAS 216758-20-2), the lipid messenger ceramide, is converted to glucosylceramide by glucosylceramide synthase (GCS). In the reverse direction, non-<wbr />lysosomal glucosylceramidase (GCase), also known as β-<wbr />glucosidase 2 (BGD), cleaves the glucosyl moiety from glucosylceramide, liberating ceramide, which can be converted into sphingomyelin. AMP-<wbr />deoxynojirimycin (AMP-<wbr />dNM) is a hydrophobic derivative of dNM. It potently inhibits BGD (IC50 = 0.3 nM), less potently antagonizes GCS (IC50 = 25 nM), but only poorly inhibits other GCase isoforms. AMP-<wbr />dNM has been shown to strongly suppress inflammation in a murine model of hapten-<wbr />induced colitis, enhance insulin sensitivity in murine and rat models of insulin resistance, and induce sterol regulatory element-<wbr />binding protein-<wbr />regulated gene expression and cholesterol synthesis in HepG2 cells.

Reference

1.Bijl, N.,Scheij, S.,Houten, S., et al. The glucosylceramide synthase inhibitor N-(5-adamantane-1-yl-methoxy-pentyl)-deoxynojirimycin induces sterol regulatory element-binding protein-regulated gene expression and cholesterol synthesis in HepG2 cells. Jo