Chemical Synthesis of d-glycero-d-manno-Heptose 1,7-Bisphosphate and Evaluation of Its Ability to Modulate NF-κB Activation
| Autor: | Yukari Fujimoto, Shinsuke Inuki, Taishin Akiyama, Shota Kawakami, Jun-ichiro Inoue, Toshihiko Aiba |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Anomer 010405 organic chemistry Chemistry Stereochemistry Organic Chemistry Heptose 010402 general chemistry Phosphate 01 natural sciences Biochemistry Chemical synthesis 0104 chemical sciences chemistry.chemical_compound Glycolipid Mitsunobu reaction Physical and Theoretical Chemistry Signal transduction Glycoprotein |
| Zdroj: | Organic letters. 19(12) |
| ISSN: | 1523-7052 |
| Popis: | d-glycero-d-manno-Heptose 1,7-bisphosphate (HBP) is the precursor for heptose residues found in Gram-negative bacterial membrane surface glycoproteins and glycolipids. HBP β-anomer was recently reported to be a pathogen-associated molecular pattern (PAMP) that regulates TIFA-dependent immunity. Herein, we report the chemical synthesis of HBP α- and β-anomers, which highlights a C-7 carbon homologation via the Corey–Chaykovsky reaction, and the introduction of a phosphate group at the anomeric position using the Mitsunobu reaction. Furthermore, NF-κB reporter assaying revealed that HBP β-anomer activates the NF-κB signaling pathway. |
| Databáze: | OpenAIRE |
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