Of 1-deoxynojirimycin

A new type of mechanism-based enzyme-inactivators, which are related to conduritol epoxides with respect to activation at the active site, was introduced by Tong and Ganem, " who prepared the aziridine 37 from the o-galacto analog of 1-deoxynojirimycin. Compound 37 proved to be a pp-... 

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. 

Von derOsten, C.H., Sinskey, A.J., Barbas El, C.F., Pederson, R.L., Wang, Y.F. and Wong, C.H., Use of a recombinant bacterial fructose-1,6-diphosphate aldolase in aldol reactions preparative syntheses of 1-deoxynojirimycin, 1-deoxymannojirimycin, l,4-dideoxy-l,4-imino-D-arahinitol, and fagomine. J. Am. Chem. Soc., 1989, 111, 3924. 

The 3-deoxyfluoro compound 97 (pZa 5.75) was published by Lee and coworkers222 who also synthesized the corresponding 3,6-difluoro derivative (98) of 1 -deoxynojirimycin.223,224... 

A study of anti-HIV replication effects of nearly 50 imino sugars demonstrated that A-alkyl derivatives of 1-deoxynojirimycin exhibit markedly enhanced activity when compared to the unsubstituted parent compound. In particular, compound 131... 

A model for the structural relationship of /V-butyl-1 -deoxynojirimycin (131, Scheme 33) with ceramide, the substrate of ceramide glucosyltransferase, was suggested by Butters and coworkers. They conducted a comparative investigation on a range of 14 derivatives of 1-deoxynojirimycin substituted at the ring nitrogen and/or C-l, as well as 5 pyrrolidine-type inhibitors selected by superpositioning of the iminoalditol with a portion of the ceramide structure.364... 

From the beginnings of imino sugar research and application, such lipophilic modifications as AA alkyl derivatives of 1-deoxynojirimycin and its relevant epimers have been prepared and their properties investigated. These amphiphilic compounds... 

N. Asano, K. Oseki, E. Kaneko, and K. Matsui, Enzymic synthesis of a- and p-D-glucosides of 1-deoxynojirimycin and their glycosidase inhibitory activities, Carbohydr. Res., 258 (1994) 255-266. 

E. M. S. Harris, A. E. Aleshin, L. M. Firsov, and R. B. Honzatko, Refined structure of the complex of 1-deoxynojirimycin with glucoamylase from Aspergillus awamori var. X100 to 2.4-A resolution, Biochemistry, 32 (1993) 1618—1626. 

G. Legler and H. Liedtke, Glucosylceramidase from calf spleen. Characterization of its active site with 4-n-alkylumbelliferyl P-glucosides and V-alkyl derivatives of 1-deoxynojirimycin, Biol. Chem. Hoppe Seyler, 366 (1985) 1113-1122. 

Several routes to 1-deoxygalactonojirimycin (5) have been published to date. l,5-Dideoxy-l,5-imino-D-galactitol (5), the epimer of 1-deoxynojirimycin (1) at C-4, was st synthesized by Paulsen and co-workers in 1980 [24]. These workers employed 1,6-anhydro- a-o-galactofuranose (6) as the starting material. 

In 1987 2,6-dideoxy-2,6-imino-D-g(ycero-L-gM/o-heptitol (14), a chain-extended derivative of 1-deoxynojirimycin, was synthesized as a potential glucosidase inhibitor [50] and soon thereafter extracted from the leaves of the Panamesian plant Omphalea diandra L [51]. Coined a-homonojirimycin by the discoverers, this novel type of inhibitor exhibited pronounced activity against gluco-... 

The L-fuco analogue of 1-deoxynojirimycin, l,5-dideoxy-l,5-imino-L-fucitol or 1-deoxy-L-fuconojirimycin (51), was first synthesized by Fleet and co-workers in 1985 by a multi-step sequence starting from methyl-a-o-glucopyranoside... 

Reproduced from Szolcsanyi, P. Gracza, T. Koman, M. Pronayova, N. Liptaj, T. Pd(ll)-catalysed aminocarbonyiation as a key step in the total synthesis of C-6 homologues of 1-deoxynojirimycin and 1-deoxy-/-idonojirimycin. Tetrahedron Asymmetry 2000, 11, 2579-2597, with permission from Elsevier. 

Various open-chain analogues [74] of 1-deoxynojirimycin, such as (32), were synthesized as potential glucosidase inhibitors and, surprisingly, exhibited good... 

SC3793> and of bromine in the synthesis of 1-deoxynojirimycin and 1-deoxymannojirimycin <07TL3115> and azabicyclic derivatives <07T5056>. 

M. Shiozaki, O. Ubukata, H. Hamyama, and R. Yoshiike, Synthesis of 1-deoxynojirimycin-trehala-mine fused compound and its related compounds, Tetrahedron Lett., 39 (1998) 1925—1928. 

M. Shiozaki, R. Yoshiike, O. Ando, O. Ubukata, and H. Hamyama, Syntheses of 1-deoxynojirimycin-trehalamine-fused and -linked compounds and their biological activities, Tetrahedron, 54 (1998) 15167-15182. 

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...

Of nearly 50 iminosugars probed for antiHIV activity [183], five were active at subcytotoxic levels. In particular, the a-glucosidase inhibitors 1-deoxynojirimycin 2 and the plant alkaloid castanospermine 4 were confirmed to be active at concentrations between 0.1 and 0.5 mg/ml. Even more pronounced were the activities of 1-deoxynojirimycin derivatives with enhanced lipophilic character such as V-methyl- 70, V-ethyl- 71 and, in particular, V-butyl-1-deoxynojirimycin 72 in the same concentration range [183,186]. 

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