Synthesis of aminoacylated ergosterols: A new lipid component of fungi

Daisuke Yokokawa; Shunsuke Tatematsu; Ryoka Takagi; Yusuke Saga; Hervé Roy; Frédéric Fischer; Hubert D Becker; Tetsuo Kushiro

doi:10.1016/j.steroids.2021.108823

Synthesis of aminoacylated ergosterols: A new lipid component of fungi

Steroids. 2021 May:169:108823. doi: 10.1016/j.steroids.2021.108823. Epub 2021 Mar 11.

Authors

Daisuke Yokokawa¹, Shunsuke Tatematsu¹, Ryoka Takagi¹, Yusuke Saga¹, Hervé Roy², Frédéric Fischer³, Hubert D Becker³, Tetsuo Kushiro⁴

Affiliations

¹ Graduate School of Agriculture, Meiji University, Kawasaki, Kanagawa 214-8571, Japan.
² Burnett School of Biomedical Sciences, College of Medicine, University of Central Florida, Orlando, FL 32826, USA.
³ Université de Strasbourg, CNRS, Génétique Moléculaire, Génomique, Microbiologie, UMR 7156, 67084 Strasbourg Cedex, France.
⁴ Graduate School of Agriculture, Meiji University, Kawasaki, Kanagawa 214-8571, Japan. Electronic address: kushiro@meiji.ac.jp.

PMID: 33713678
DOI: 10.1016/j.steroids.2021.108823

Abstract

Aminoacylated ergosterol such as 1-ergosteryl aspartate (Erg-Asp) is a new lipid component recently discovered in fungi. In order to study physiological functions of this novel sterol derivative and to develop potential antifungal agents, we established the method to synthesize aminoacylated ergosterol derivatives. Herein, we report the synthesis of Erg-Asp as well as some other aminoacylated ergosterols (Erg-Gly, Erg-Ala, Erg-Leu, Erg-Ile, and Erg-Val) using Boc protected amino acids.

Keywords: 1-Ergosteryl aspartate; Aminoacylated sterol; Ergosterol; Fungi.

MeSH terms

Acylation
Amino Acids / chemical synthesis
Amino Acids / chemistry
Chemistry Techniques, Synthetic
Ergosterol* / chemical synthesis
Ergosterol* / chemistry
Fungi*

Substances

Ergosterol
Amino Acids

Grants and funding

R21 AI144481/AI/NIAID NIH HHS/United States