2905. 1-Deoxynojirimycin

Nomenclature

CAS number: 19130-96-2
(2R,3R,4R,5S)-2-(Hydroxymethyl)-3,4,5-piperidinetriol; 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; Bay n 5595; S-GI.
C6H13NO4; mol wt 163.17.
C 44.17%, H 8.03%, N 8.58%, O 39.22%.

Description and references

α-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 α-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).

Chemical structure

Properties

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