title: Preparation of a fluorous protecting group and its application to the chemoenzymatic synthesis of sialidase inhibitor.
abstract: 2-(Perfluorohexyl)ethoxymethyl chloride was prepared as a novel fluorous protecting reagent. Neu5Ac aldolase-catalyzed chemoenzymatic transformation of N-acetyl-D-mannosamine to Neu5Ac derivatives was achieved successfully by using the fluorous reagent not only for hydroxy group protection but also for fluorous tagging. This chemoenzymatic method was applied to the synthesis of 2-deoxy-2,3-didehydrosialic acid 1 known as a potent sialidase inhibitor.
authors.affiliation: Department of Organic Chemistry, School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada Suruga-Ku, Shizuoka, 422-8526, Japan. ikeda@ys2.u-shizuoka-ken.ac.jp
authors.forename: Kiyoshi
authors.initials: K
authors.lastname: Ikeda
authors.forename: Hitomi
authors.initials: H
authors.lastname: Mori
authors.forename: Masayuki
authors.initials: M
authors.lastname: Sato
mesh_terms: D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006595:Hexosamines / Q000737:chemistry; D015394:Molecular Structure; D019158:N-Acetylneuraminic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D009439:Neuraminidase / Q000037:antagonists & inhibitors*; D007652:Oxo-Acid-Lyases / Q000378:metabolism*
chemical_list: D004791:Enzyme Inhibitors; D006595:Hexosamines; C036137:2-deoxy-2,3-dehydro-N-acetylneuraminic acid; D009439:Neuraminidase; D007652:Oxo-Acid-Lyases; C018728:N-acetylneuraminate lyase; D019158:N-Acetylneuraminic Acid; C002022:N-acetylmannosamine