I- Deoxynojirimycin

From leaves of Moms bombycis and from Moms alba (white mulberry). Powder. Md + 118.8 (c, 0.1 in H2O). I -O-P-D-Glucopyrimoside 6-O-fi-D-Gbicopyranosyl-I-deoxynojirimycin [156714-96-4]... 

A short route to A -benzyl-I-deoxynojirimycin by a double reductive amination of D-o /o-hexos-5-ulose (S-fe/o-D-glucose) with benzylamine has been desaibed. In a similar way reductive amination with various amines and D-r/ireo-hex-2,S-diuIose (S-Aeto-D-fructose) gives 2,S-anhydro-2,S-iminoaIditoIs. ... 

Romaniouk, A.V., Silva, A., Feng, J., and Vijay, I.K. (2004) Synthesis of a novel photoaffinity derivative of 1-deoxynojirimycin for active site-directed labeling of I. Glycobiology 14, 301-310. 

Hi) Castanospermine Versus 1-Deoxynojirimycin. The seemingly rigid castanospermine structure28 was found in a 1/1/i boat (carbohydrate numbering) when complexed with the exo-l,3-p-glucanase from Candida albicans, a family GH 5 enzyme (PDB 1EQC).273... 

S. M. Andersen, M. Ebner, C. W. Ekhart, G. Gradnig, G. Legler, I. Lundt, A. E. Stiitz, S. G. Withers, and T. Wrodnigg, Two isosteric fluorinated derivatives of the powerful glucosidase inhibitors, 1-deoxynojirimycin and 2,5-dideoxy-2,5-imino-D-mannitol Syntheses and glycosidase inhibitory activities of l,2,5-trideoxy-2-fluoro-l,5-imino-D-glucitol and of l,2,5-trideoxy-l-fluoro-2,5-imino-D-mannitol, Carbohydr. Res., 301 (1997) 155-166. 

B. Brumshtein, H. M. Greenblatt, T. D. Butters, Y. Shaaltiel, D. Aviezer, I. Sihnan, A. H. Futerman, and J. L. Sussman, Crystal structures of complexes of iV-butyl- and iV-nonyl-deoxynojirimycin bound to acid P-glucosidase. Insights into the mechanism of chemical chaperone action in Gaucher disease,... 

L. Yu, K. Ikeda, A. Kato, I. Adachi, G. Godin, P. Compain, O. Martin, and N. Asano, a-l-C-Octyl-1-deoxynojirimycin as a pharmacological chaperone for Gaucher disease, Bioorg. Med. Chem., 14 (2006) 7736-7744. 

The isoxazoline-furanose intermediate derived from h/i(hydroxylation) was also submitted to direct hydrogenation. The reduction proceeded in a highly diaster-eoselective manner at the C=N double bond. In the gluco series starting with 150, several deoxynojirimycin analogues with extended side chains at C-5 (carbohydrate numbering) such as 151 were obtained by this method (23,313,314). Eurther conversion of 151 led to indolizidine polyols (1,4,8-trideoxyimino polyols), which... 

Scheme 10. Biosynthetic formation of 1-deoxynojirimycin (18) and mannojirimycin (19). Note the inversion of the label (the 1 -label becomes a 6-label), i. e., the 5-deoxygenation is really a 2-deoxygenation...

Figure 6 Chemical tools can be used to interfere with cellular glycosylation. Tools to interfere with mucin-type 0-linked glycosylation include (a) a-benzyl GalNAc (b) Galpl-4GlcNAcp-0-naphthalenemethanol (c) Galpl-3GlcNAcp-0-naphthalenemethanol (d) 1-68A and (e) 2-68A. Molecules used to disrupt N-linked glycosylation at different steps include (f) 1-deoxymannojirimycin (g) deoxynojirimycin (h) tunicamycin and (i) swainsonine.

Deoxynojirimycin (DNJ) potent inhibitor of a-glucosidases (including trehalase, invertase, sucrase, maltase, isomaltase), more weakly inhibitory to Glucosidase I and II, and p-glucosidases, also (x-mannosidases, a-fucosidase, a- and p-galactosidases (including lactase) - "... 

Cox, T., Lachmann, R., Hollak, C., Aerts, X, van Weely, S., FIrebicek, M., Platt, F., Bntters, T., Dwek, R., Moyses, C., Gow, I., Hstein, D., Zimran, A. Novel oral treatment of Gaucher s disease with N-butyl-deoxynojirimycin (OGT 918) to decrease substrate biosynthesis. Lancet 2000 355 1481-1485... 

Synthesis from i-threose Nojirimycin (1) and 1-deoxynojirimycin (2) have been synthesized from 4-6 -( err-butyldimethylsilyl)-2,3-0-isopropylidene-L-threose (118) (Scheme 22) Compound 118 was treated with trimethyl phosphonoacetate to provide the E ester 119, as a single isomer in 95% yield. Reduction of the ester group in 119 followed by Sharpless asymmetric epoxidation of the resulting allylic alcohol afforded the syn-epoxide 120. Treatment of 120 with NaNs and NH4CI in a mixture of 1,2-dimethoxyethane,... 

Piperidine 1-Deoxynojirimycin (38), 1-Deoxymannojirimycin (39), o-Homonojirimycin (40) Omf alea diandra HIV Glucosidase I Mannosidase 1 [12, 38]... 

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