Synthesis of 12- O-Mono- and Diglycosyl-oxystearates, a New Class of Agonists for the C-type Lectin Receptor Mincle

Le Van Huy; Chiaki Tanaka; Takashi Imai; Sho Yamasaki; Tomofumi Miyamoto

doi:10.1021/acsmedchemlett.8b00413

Synthesis of 12- O-Mono- and Diglycosyl-oxystearates, a New Class of Agonists for the C-type Lectin Receptor Mincle

ACS Med Chem Lett. 2018 Dec 13;10(1):44-49. doi: 10.1021/acsmedchemlett.8b00413. eCollection 2019 Jan 10.

Authors

Le Van Huy¹, Chiaki Tanaka¹, Takashi Imai², Sho Yamasaki², Tomofumi Miyamoto¹

Affiliations

¹ Department of Natural Products Chemistry, Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582, Japan.
² Department of Molecular Immunology, Immunology Frontier Research Center, Osaka University, Osaka 565-0871, Japan.

Abstract

Fifteen glycosyl-oxystearates were synthesized by Crich's 4,6-benzylidene and Köening-Knorr strategies. Assessment of structure-activity relationships using macrophage-inducible C-type lectin (Mincle) receptor cells expressing nuclear factor of activated T cells (NFAT)-green fluorescent protein (GFP) revealed that four dimannopyranosyl-oxystearate analogues were Mincle agonists and that 12-O-(2-O-α-d-mannopyranosyl)-α-d-mannopyranosyl-oxystearate was as an activator of both mouse and human Mincle.