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

Toshihiko Aiba, Masaki Sato, Daichi Umegaki, Takanori Iwasaki, Nobuaki Kambe, Koichi Fukase, Yukari Fujimoto

Research output: Contribution to journalArticle

16 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)6672-6675
Number of pages4
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number28
DOIs
Publication statusPublished - 2016

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

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