title: Synthetic study of 3-fluorinated sialic acid derivatives.
abstract: Sialic acid derivatives, analogs, and their conjugates are expected to be pharmaceutical candidates such as anti-influenza drugs and also useful probes for investigating the biological role of glycoconjugates. Derivatives of 3-fluorinated sialic acid (3-F-Sia) have been found to be excellent probes in investigating functions and mechanisms of a series of proteins. Here, we describe the syntheses of 3-F-Sia derivatives, which are useful in making biologically important conjugate probes. A practical method for the construction of 3-fluorinated sialosides based on the stereoselective formation of the corresponding anomeric O-trimethylsilyl ether and their nucleophilic attack by an alkyl halide, an allyl halide in particular, was developed. In addition, details of the synthesis of cytidine monophosphate (CMP)-3-F-Sia bearing a fluorescent tag, which has been proven to show dual functions as a substrate of CMP-sialic acid transporter (CST) and an inhibitor of sialyltransferase (STase), are described.
authors: ERATO, Japan Science and Technology Agency (JST), 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
authors: Katsuhiko
authors: K
authors: Suzuki
authors: ERATO, Japan Science and Technology Agency (JST), 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
authors: Shusaku
authors: S
authors: Daikoku
authors: ERATO, Japan Science and Technology Agency (JST), 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
authors: Sang-Hyun
authors: SH
authors: Son
authors: ERATO, Japan Science and Technology Agency (JST), 2-1 Hirosawa, Wako, Saitama 351-0198, Japan; Synthetic Cellular Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
authors: Yukishige
authors: Y
authors: Ito
authors: ERATO, Japan Science and Technology Agency (JST), 2-1 Hirosawa, Wako, Saitama 351-0198, Japan; Institute of Glycoscience, Tokai University, 4-1-1 Kitakaname, Hiratsuka, Kanagawa 259-1292, Japan. Electronic address: kanie@tokai-u.jp.
authors: Osamu
authors: O
authors: Kanie
mesh_terms: D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D005456:Fluorescent Dyes / Q000138:chemical synthesis; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis*; D015335:Molecular Probes / Q000138:chemical synthesis*; D012794:Sialic Acids / Q000138:chemical synthesis*; D012799:Sialyltransferases / Q000037:antagonists & inhibitors; D013237:Stereoisomerism
chemical_list: D004791:Enzyme Inhibitors; D005456:Fluorescent Dyes; D006845:Hydrocarbons, Fluorinated; D015335:Molecular Probes; D012794:Sialic Acids; D012799:Sialyltransferases
keywords: Alkylation; Glycosides; Inhibitor; Substrate