To probe the utility of a multivalent approach for fucosidase inhibition, a series of di‐ and tri‐valent imino sugars based on L‐fuco‐configured 1,4‐imino‐ and 1,4‐bis(imino)‐cyclitol epitopes has been synthesized and analyzed for fucosidase inhibition with the best trivalent species yielding a modest improvement in binding constant. Structural analysis of a representative pair of mono‐ and tri‐valent imino sugars has been performed on a bacterial fucosidase, BtFuc2970. The 3D structures show binding of the imino‐cyclitol in the 3E conformation, consistent with the known pathway for fucosidase action.
A review dealing with iminosugars as inhibitors of -L-fucosidases is presented. The different synthetic approaches for the preparation of the most relevant ones as well as their inhibitory properties are presented.
The synthesis of α/β-L-fucosylated cysteamine, 3-thiopropionic acid, and 3-thioacetic acid derivatives as building blocks for the preparation of S-neofucopeptides is shown. These compounds were used in the synthesis of new thiofucosides derivatives (8α, 9α, 9β, 10α, 22α, 22β, 24α, 26α) that
A new furyl amino acid derivative was trimerized to give a linear peptide and finally was cyclized. The newly generated cyclopeptide was subjected to a conformational study in order to be considered as a C 3 -symmetric platform for the ratio-
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.