TY - JOUR
T1 - Regioselective phosphorylation of
T2 - Myo -inositol with BINOL-derived phosphoramidites and its application for protozoan lysophosphatidylinositol
AU - Aiba, Toshihiko
AU - Sato, Masaki
AU - Umegaki, Daichi
AU - Iwasaki, Takanori
AU - Kambe, Nobuaki
AU - Fukase, Koichi
AU - Fujimoto, Yukari
N1 - Funding Information:
This work was supported in part by Grants-in-Aid for Scientific Research (no. 26282211 and 26102732) from the Japan Society for the Promotion of Science, by ERATO Murata Lipid Active Structure Project, by a funding program for Next Generation World- Leading Researchers (NEXT Program; LR025) from JSPS and CSTP, by Keio Gijuku Academic Development Funds, by Yamada Science Foundation, and by The Sumitomo Foundation.
Publisher Copyright:
© 2016 The Royal Society of Chemistry.
PY - 2016
Y1 - 2016
N2 - 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.
AB - 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.
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U2 - 10.1039/c6ob01062h
DO - 10.1039/c6ob01062h
M3 - Article
C2 - 27326923
AN - SCOPUS:84978886158
SN - 1477-0520
VL - 14
SP - 6672
EP - 6675
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 28
ER -