Aiba T, Sato M, Umegaki D, Iwasaki T, Kambe N, Fujimoto Y Regioselective phosphorylation of myo-inositol with BINOL-derived phosphoramidites and its application for protozoan lysophosphatidylinositol Organic and Biomolecular Chemistry14(28) (2016)
6672-6675
/Variants 0/-+
|
L-myoIno-(1--P--1)--R-Gro
/Variants 0/ is:
84%Mon-(1-3)-
OR (exclusively)
16%LIP-(1-3)-
NCBI PubMed ID:27326923 Publication DOI:10.1039/c6ob01062h Journal NLM ID:101154995 Publisher: The Royal Society of Chemistry Correspondence: fujimotoychem.keio.ac.jp Institutions: Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan, Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan, Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan
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.
Found 
report error
chem.keio.ac.jp