Regioselective phosphorylation of myo-inositol with BINOL-derived phosphoramidites and its application for protozoan lysophosphatidylinositol.
A regioselective phosphorylation method for myo-inositol was developed by utilizing readily preparable BINOL-derived phosphoramidites. The method also facilitated the complete separation of the diastereomeric products by simple chromatography. Based on this phosphorylation and Ni-catalyzed alkyl-alkyl cross-coupling reaction for long fatty acids, we achieved the first synthesis of a lysophosphatidylinositol, EhPIa having long fatty acid C30:1, as a partial structure of glycosylphosphatidylinositol (GPI) anchor from the cell membrane of a protozoa, Entamoeba histolytica.
Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan. fujimotoy@chem.keio.ac.jp and Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
Toshihiko
T
Aiba
Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan. fujimotoy@chem.keio.ac.jp.
Masaki
M
Sato
Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan. fujimotoy@chem.keio.ac.jp.
Daichi
D
Umegaki
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.
Takanori
T
Iwasaki
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.
Nobuaki
N
Kambe
Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan. fujimotoy@chem.keio.ac.jp.
Koichi
K
Fukase
Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan. fujimotoy@chem.keio.ac.jp and Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
Yukari
Y
Fujimoto
D002384:Catalysis; D004748:Entamoeba histolytica / Q000737:chemistry*; D017261:Glycosylphosphatidylinositols / Q000138:chemical synthesis / Q000737:chemistry; D007294:Inositol / Q000138:chemical synthesis / Q000737:chemistry*; D008246:Lysophospholipids / Q000138:chemical synthesis* / Q000737:chemistry; D009284:Naphthols / Q000737:chemistry*; D009532:Nickel / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
C406944:BINOL, naphthol; D017261:Glycosylphosphatidylinositols; D008246:Lysophospholipids; D009284:Naphthols; D009943:Organophosphorus Compounds; C025449:lysophosphatidylinositol; C434331:phosphoramidite; D007294:Inositol; D009532:Nickel