Aldolases 1-deoxynojirimycin, preparation

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. 

C. H. von der Osten, A. Sinskey, C. F. Barbas, R. L. Pederson, Y.-F. Wang, and C.-H. Wong, Use of a recombinant bacterial fractose-l,6-diphospbate aldolase in aldol reactions Preparative syntheses of 1-deoxynojirimycin, 1-deoxymannoijirimycin, 1,4-imino-D-arabinitol, and fago-mine, J. Am. Chem. Soc. 777 3924 (1989). 

A combined enzymatic/chemical synthesis of imino-alditols used fructose 1,6-diphosphate aldolase to generate 6-azido-ketohexoses (as outlined in Scheme 4) which could be catalytically reduced to deoxynojirimycin and deoxymannojirimycin. By use of appropriate azido-aldehydes, fagomine(15) and 1,4-dideoxy-l,4-imino-D-arabinitol (16) were similarly prepared. Microbial epimerization of 1-deoxy-... 

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