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

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 inn...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2020-05, Vol.18 (19), p.3659-3663
Main Authors: Arai, Yohei, Torigoe, Shota, Matsumaru, Takanori, Yamasaki, Sho, Fujimoto, Yukari
Format: Article
Language:English
Subjects:
Agonists
Immunomodulation
Inositol
Phosphatidylinositol
Phosphorylation
Synthesis
Tuberculosis
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob02724f