Deoxy-DMDP

Examples of other fluorinated inhibitors, mainly of D-glucosidases, are the 2-deoxy-2-fluoro derivative 106 (Scheme 27) of miglitol (A-hydroxyethy I -1 -deoxynoj i i i my-cin, 107),229 4-deoxy-4,4-difluoroisofagomine (108),230 3-deoxy-3-fluoro-calystegin B2 (109),231 the 1-deoxyfluoro derivative (110) of 2,5-dideoxy-2,5-imino-D-mann-itol,232 as well as the 3-deoxyfluoro analogue (111) of nonnatural l-DMDP (2,5-dideoxy-2,5-imino-L-mannitol)233 and the 3-deoxy-3,3-difluoro derivative (112) of 2,5-dideoxy-2,5-imino-D-glucitol (113).234 All of these are weaker inhibitors than the parent compounds. l,4,6-Trideoxy-6-fluoro-l,4-imino-D-mannitol (114) was prepared by Winchester and coworkers.210... 

The most significant indication that the biocatalytic properties also depend on the expression host comes from our studies on the fructose analogues DMDP 10 (2,5-dihydroxymethyl-(3S,4R)-dihydroxypyrrolidine) and 5-deoxy-D-fructose as inhibitors of SuSyl (Fig. 2.2.6.2). In contrast to SuSyl from yeast, the strongest inhibitor for recombinant SuSyl from E. coli is 10 (IC501.5 mM), suggesting that the enzyme prefers the D-fructofuranose conformation. 

Deoxy-6-C-(2,5-dihydroxyhexyl)-DMDP Hyacinthoides non-scripta (Hyadnthaceae) fruits/stalks Scilla campanulata (Hyacinthaceae) bulb ... 

Deoxy-6-C-(2,5- dihydroxyhexyD-DMDP moderate inhibitor of amyloglucosidase and weak inhibitor of a-fucosidase"... 

---