title: The spirocyclopropyl moiety as a methyl surrogate in the structure of l-fucosidase and l-rhamnosidase inhibitors.
abstract: Nitrogen-in-the-ring analogues of l-fucose and l-rhamnose were prepared, which feature a spirocyclopropyl moiety in place of the methyl group of the natural sugar. The synthetic route involved a titanium-mediated aminocyclopropanation of a glycononitrile as the key step. Four new spirocyclopropyl iminosugar analogues were generated, which displayed some activity towards l-fucosidase and l-rhamnosidase.
authors.affiliation: Université de Reims Champagne-Ardenne, Institut de Chimie Moléculaire de Reims, CNRS UMR 6229, UFR des Sciences Exactes et Naturelles, BP 1039, 51687 Reims Cedex 2, France.
authors.forename: Morwenna S M
authors.initials: MS
authors.lastname: Pearson
authors.forename: Nicolas
authors.initials: N
authors.lastname: Floquet
authors.forename: Claudia
authors.initials: C
authors.lastname: Bello
authors.forename: Pierre
authors.initials: P
authors.lastname: Vogel
authors.forename: Richard
authors.initials: R
authors.lastname: Plantier-Royon
authors.forename: Jan
authors.initials: J
authors.lastname: Szymoniak
authors.forename: Philippe
authors.initials: P
authors.lastname: Bertus
authors.forename: Jean-Bernard
authors.initials: JB
authors.lastname: Behr
mesh_terms: D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005643:Fucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors / Q000378:metabolism; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D009904:Optical Rotation; D012210:Rhamnose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D021241:Spectrometry, Mass, Electrospray Ionization; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005644:alpha-L-Fucosidase / Q000037:antagonists & inhibitors / Q000378:metabolism
chemical_list: D003521:Cyclopropanes; D004791:Enzyme Inhibitors; D013141:Spiro Compounds; D005643:Fucose; D006026:Glycoside Hydrolases; C022525:alpha-L-rhamnosidase; D005644:alpha-L-Fucosidase; D012210:Rhamnose