82300-58-1Relevant articles and documents
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
, p. 3079 - 3082 (2017/06/23)
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.
Synthesis of Glycosyl Phosphates Using the Fraser-Reid Activation
Pale, Patrick,Whitesides, George M.
, p. 4547 - 4549 (2007/10/02)
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Glycosyl Imidates, 10. - Glycosyl Phosphates from Glycosyl Trichloroacetimidates
Schmidt, Richard R.,Stumpp, Michael
, p. 680 - 691 (2007/10/02)
The glycosyl trichloroacetimidates 1-α,β, 8-α, 11-α, 13-α, 15-α, and 17-α directly transfer the glycosyl moiety to phosphoric acid mono- and diesters.The acidity of the phosphoric acid derivatives used was sufficient for the activation of the trichloroacetimidates, therefore an additional acidic catalyst was not required.From the β-imidate 1-β α-glycosyl phosphate and from the α-imidates preferentially β-glycosyl phosphates were obtained.Reaction of dibenzyl phosphate (2a) and cetyl phosphate (2c) with 1-α demonstrated that β/α-anomerization iscatalyzed by traces of acid.The glycosyl phosphates 3a-α, 3a-β - 3c-β, 3f-α, 9a-β, and 9c-β were partly or totally deprotected.The structures of the synthezised compounds were assigned by 1H NMR spectroscopy and by comparison with literature data.
