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

作者：Takanori Matsumaru, Kasumi Sakuratani, Saeko Yanaka, Koichi Kato, Sho Yamasaki, Yukari Fujimoto · 发表于：European Journal of Organic Chemistry · 年份：2022 · DOI：10.1002/ejoc.202200109 · 被引用次数：4 · 研究领域：Microbial Natural Products and Biosynthesis、Glycosylation and Glycoproteins Research、Antimicrobial Peptides and Activities

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.