Fungal β-Mannosyloxymannitol Glycolipids and Their Analogues: Synthesis and Mincle-Mediated Signaling Activity

Takanori Matsumaru, Kasumi Sakuratani, Saeko Yanaka, Koichi Kato, Sho Yamasaki, Yukari Fujimoto

Research output: Contribution to journalArticlepeer-review

Abstract

Mincle, a C-type lectin receptor (CLR), senses certain lipid conjugates, leading to the activation of the innate immune system. The lipid conjugate ligands include glyco-, glycero-, and mannitol lipids. Recently, a fungal β-mannosyloxymannitol glycolipid demonstrating a novel architecture, “44-2,” was isolated from the fungus Malassezia and displayed potent Mincle-mediated signaling activity. For this study, we synthesized the diastereomeric pair of mannosyloxymannitol glycolipids and their analogues and analyzed the structure-activity relationships of Mincle-mediated signaling. The results suggest that the dimannosyl-fatty acid moiety in the mannosyloxymannitol glycolipid-type structure plays a major role in the molecular recognition of Mincle.

Original languageEnglish
Article numbere202200109
JournalEuropean Journal of Organic Chemistry
Volume2022
Issue number20
DOIs
Publication statusPublished - 2022 May 25

Keywords

  • C-Type lectin receptor
  • Innate immunity
  • Lipid conjugates
  • Mincle
  • Natural products

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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