Preparation of a fluorous protecting group and its application to the chemoenzymatic synthesis of sialidase inhibitor.
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.
Ikeda
Kiyoshi
K
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
Mori
Hitomi
H
Sato
Masayuki
M
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*
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