1-Deoxynojirimycin

1-脱氧野尻霉素,

Glucose analog and potent inhibitor of α-glucosidases of class I and II. It interferes with N-linked glycosylation and oligosaccharide processing. The compound inhibits intestinal α-glucosidase and has protective effects against obesity-induced hepatic injury as well as mitochondrial dysfunction. It also has neuroprotective effects since it reduces senescence-related cognitive impairment, neuroinflammation and amyloid beta deposition in mice.

1-Deoxynojirimycin (1-dNM), produced by Bacillus species, is a glucose analog that potently inhibits α-glucosidase I and II. It prevents the formation of complex N-linked oligosaccharides in yeast and intact mammalian cells by inhibiting both α-glucosidase I and II with IC50 values of ~2 µM. 1-dNM, at a concentration of 0.4 mM, is reported to inhibit virus spread in HIV-infected lymphocyte cultures by interfering with α-glucosidase activity.

1-Deoxynojirimycin, also known as antibiotic S-gi or moranoline, belongs to the class of organic compounds known as piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms. 1-Deoxynojirimycin exists as a solid, soluble (in water), and a very weakly acidic compound (based on its pKa). Within the cell, 1-deoxynojirimycin is primarily located in the cytoplasm. Outside of the human body, 1-deoxynojirimycin can be found in fruits. This makes 1-deoxynojirimycin a potential biomarker for the consumption of this food product.

Title: 1-Deoxynojirimycin

CAS Registry Number: 19130-96-2

CAS Name: (2R,3R,4R,5S)-2-(Hydroxymethyl)-3,4,5-piperidinetriol

Additional Names: D-5-amino-1,5-dideoxyglucopyranose; 1,5-dideoxy-1,5-imino-D-glucitol; (2R,3R,4R,5S)-2-hydroxymethyl-3,4,5-trihydroxypiperidine; moranoline

Manufacturers' Codes: Bay n 5595; S-GI

Molecular Formula: C6H13NO4

Molecular Weight: 163.17

Percent Composition: C 44.17%, H 8.03%, N 8.58%, O 39.22%

Literature References: a-Glucosidase inhibitor. Prepd by reduction of nojirimycin: S. Inouye et al., J. Antibiot. 19A, 290 (1966); S. Inouye et al., Tetrahedron 23, 2125 (1968). Isoln from mulberry, Morus spp. (Moraceae): M. Yagi et al., Nippon Nogei Kagaku Kaishi 50, 571 (1976), C.A. 86, 167851r (1977). Production by Bacillus subtilis DSM704: D. C. Stein et al., Appl. Environ. Microbiol. 48, 280 (1984). Total synthesis: H. Setoi et al., Chem. Pharm. Bull. 34, 2642 (1986); H. J. G. Broxterman et al., Rec. Trav. Chim. 106, 571 (1987). HPLC determn: M. D. Cole et al., J. Chromatogr. 445, 295 (1988). Inhibition of a-glucosidase: Y. Yoshikuni, Agric. Biol. Chem. 52, 121 (1988). Antiviral activity: P. S. Sunkara et al., Biochem. Biophys. Res. Commun. 148, 206 (1987). Inhibition of glycoprotein synthesis and secretion: N. Peyrieras et al., EMBO J. 2, 823 (1983); V. Gross et al., Biochem. J. 236, 853 (1986); M. Bollen et al., Biochem. Pharmacol. 37, 905 (1988).

Properties: Prisms from water/ethanol, mp 195°. [a]D21 +47° (c = 1.045 in water); [a]D20 +46.7° (c = 0.2 in water); [a]D20 +36° (c = 0.02 in water). pKa 6.6.

Melting point: mp 195°

pKa: pKa 6.6

Optical Rotation: [a]D21 +47° (c = 1.045 in water); [a]D20 +46.7° (c = 0.2 in water); [a]D20 +36° (c = 0.02 in water)