Chemical Synthesis of d -glycero- d -manno-Heptose 1,7-Bisphosphate and Evaluation of Its Ability to Modulate NF-κB Activation

Shinsuke Inuki, Toshihiko Aiba, Shota Kawakami, Taishin Akiyama, Jun Ichiro Inoue, Yukari Fujimoto

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)3079-3082
Number of pages4
JournalOrganic Letters
Volume19
Issue number12
DOIs
Publication statusPublished - 2017 Jun 16

Fingerprint

Heptoses
Membrane Glycoproteins
Chemical activation
assaying
activation
pathogens
evaluation
Glycolipids
immunity
synthesis
Immunity
phosphates
Carbon
Phosphates
membranes
Membranes
carbon
glycero-manno-heptose

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Chemical Synthesis of d -glycero- d -manno-Heptose 1,7-Bisphosphate and Evaluation of Its Ability to Modulate NF-κB Activation. / Inuki, Shinsuke; Aiba, Toshihiko; Kawakami, Shota; Akiyama, Taishin; Inoue, Jun Ichiro; Fujimoto, Yukari.

In: Organic Letters, Vol. 19, No. 12, 16.06.2017, p. 3079-3082.

Research output: Contribution to journalArticle

Inuki, Shinsuke ; Aiba, Toshihiko ; Kawakami, Shota ; Akiyama, Taishin ; Inoue, Jun Ichiro ; Fujimoto, Yukari. / Chemical Synthesis of d -glycero- d -manno-Heptose 1,7-Bisphosphate and Evaluation of Its Ability to Modulate NF-κB Activation. In: Organic Letters. 2017 ; Vol. 19, No. 12. pp. 3079-3082.
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