Issue 28, 2016

Regioselective phosphorylation of myo-inositol with BINOL-derived phosphoramidites and its application for protozoan lysophosphatidylinositol

Abstract

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.

Graphical abstract: Regioselective phosphorylation of myo-inositol with BINOL-derived phosphoramidites and its application for protozoan lysophosphatidylinositol

Supplementary files

Article information

Article type
Communication
Submitted
16 May 2016
Accepted
07 Jun 2016
First published
07 Jun 2016

Org. Biomol. Chem., 2016,14, 6672-6675

Regioselective phosphorylation of myo-inositol with BINOL-derived phosphoramidites and its application for protozoan lysophosphatidylinositol

T. Aiba, M. Sato, D. Umegaki, T. Iwasaki, N. Kambe, K. Fukase and Y. Fujimoto, Org. Biomol. Chem., 2016, 14, 6672 DOI: 10.1039/C6OB01062H

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