Synthesis of an α-Fucosidase Inhibitor, 5a-Carba-β-l-fucopyranosylamine, and Fucose-Type α- and β-dl-Valienamine Unsaturated Derivatives

Synthesis and Conformational and Biological Aspects of Carbasugars

“…These activities suggest that carbasugar derivatives 114 and 115 work as chemical chaperones to accelerate transport and maturation of mutant forms of enzyme proteins and therefore may be considered as novel therapeutic agents for human genetic diseases related to lysosomal storage disorders. 112,113 5a-Carba-R-DL-fucopyranosyl amine ((()-116) 114 and 5acarba-β-L-fucopyranosylamine (117) 115 were prepared and evaluated (Figure 29) in the search for different sugar hydrolase inhibitors. They have displayed a very potent and specific inhibition of R-L-fucosidase (bovine kidney), with the effect of (()-116 being essentially comparable to that of deoxyfuconojirimicin, the most powerful mammalian R-Lfucosidase inhibitor identified.…”

Synthetic and Crystallographic Insight into Exploiting sp2 Hybridization in the Development of α‐l‐Fucosidase Inhibitors

“…All the compounds displayed activity as inhibitors against bFUCA1 ( Table 1). [26] Some trends were apparent in the relative activities of the carbamates. This is in accordance with what has been observed for other inhibitors using this scaffold to target other enzyme classes [15,18] and also for other inhibitor scaffolds trying to mimic the transition state of GH29 a-l-fucosidase-mediated reactions.…”

Biosynthesis and Biological Activity of Carbasugars

“…In the search for different sugar hydrolase inhibitors, 5a-carba--DL-fucopyranosyl amine [355,356] ((±)-167) and 5a-carba--L-fucopyranosylamine (168) [357] were prepared. These compounds have been shown to be strong inhibitors of -L-fucosidase.…”