The key entity of a DCAR agonist, phosphatidylinositol mannoside Ac1PIM1: its synthesis and immunomodulatory function

Org Biomol Chem. 2020 May 21;18(19):3659-3663. doi: 10.1039/c9ob02724f. Epub 2020 May 1.

Abstract

Ac1PIM1 is a potential biosynthetic intermediate for phosphatidylinositol mannosides (PIMs) from Mycobacterium tuberculosis. We achieved the first synthesis of Ac1PIM1 by utilizing an allyl-type protecting group strategy and regioselective phosphorylation of inositol. A very potent agonist of an innate immune receptor DCAR, which is better than previously known agonists, is demonstrated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cytokines / biosynthesis
  • Immunomodulation / drug effects*
  • Lectins, C-Type / agonists*
  • Lectins, C-Type / immunology
  • Mice
  • Mycobacterium tuberculosis / chemistry*
  • Mycobacterium tuberculosis / immunology
  • Phosphatidylinositols / chemical synthesis
  • Phosphatidylinositols / chemistry
  • Phosphatidylinositols / pharmacology*
  • Phosphorylation
  • RAW 264.7 Cells
  • Receptors, Immunologic / agonists*
  • Receptors, Immunologic / immunology

Substances

  • Cytokines
  • Lectins, C-Type
  • Phosphatidylinositols
  • Receptors, Immunologic
  • dendritic cell immunoactivating receptor, mouse
  • phosphatidylinositol mannoside