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Issue 28, 2016
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Regioselective phosphorylation of myo-inositol with BINOL-derived phosphoramidites and its application for protozoan lysophosphatidylinositol

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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

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Article information


Submitted
16 May 2016
Accepted
07 Jun 2016
First published
07 Jun 2016

Org. Biomol. Chem., 2016,14, 6672-6675
Article type
Communication

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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