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

12 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

Fingerprint

inositols
phosphorylation
Phosphorylation
Inositol
fatty acids
Fatty Acids
protozoa
Protozoa
Glycosylphosphatidylinositols
Entamoeba histolytica
cross coupling
Cross Reactions
chromatography
Cell membranes
Chromatography
Cell Membrane
synthesis
products
phosphoramidite
lysophosphatidylinositol

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

Cite this

Regioselective phosphorylation of : Myo -inositol with BINOL-derived phosphoramidites and its application for protozoan lysophosphatidylinositol. / Aiba, Toshihiko; Sato, Masaki; Umegaki, Daichi; Iwasaki, Takanori; Kambe, Nobuaki; Fukase, Koichi; Fujimoto, Yukari.

In: Organic and Biomolecular Chemistry, Vol. 14, No. 28, 2016, p. 6672-6675.

Research output: Contribution to journalArticle

Aiba, Toshihiko ; Sato, Masaki ; Umegaki, Daichi ; Iwasaki, Takanori ; Kambe, Nobuaki ; Fukase, Koichi ; Fujimoto, Yukari. / Regioselective phosphorylation of : Myo -inositol with BINOL-derived phosphoramidites and its application for protozoan lysophosphatidylinositol. In: Organic and Biomolecular Chemistry. 2016 ; Vol. 14, No. 28. pp. 6672-6675.
@article{c50c734261d24057a7cc4c968e69a1ac,
title = "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.",
author = "Toshihiko Aiba and Masaki Sato and Daichi Umegaki and Takanori Iwasaki and Nobuaki Kambe and Koichi Fukase and Yukari Fujimoto",
year = "2016",
doi = "10.1039/c6ob01062h",
language = "English",
volume = "14",
pages = "6672--6675",
journal = "Organic and Biomolecular Chemistry",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",
number = "28",

}

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

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.

UR - http://www.scopus.com/inward/record.url?scp=84978886158&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84978886158&partnerID=8YFLogxK

U2 - 10.1039/c6ob01062h

DO - 10.1039/c6ob01062h

M3 - Article

C2 - 27326923

AN - SCOPUS:84978886158

VL - 14

SP - 6672

EP - 6675

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 28

ER -