250691-64-6Relevant 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)
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.
Glycosyl iodides are highly efficient donors under neutral conditions
Hadd, Michael J.,Gervay, Jacquelyn
, p. 61 - 69 (2007/10/03)
Glycosyl iodides have been prepared and subjected to glycosylation under neutral conditions. The reactions are highly efficient, giving α glycosides even with sterically demanding glycosyl acceptors. Glucosyl iodides react with allyl alcohol slowest and require refluxing conditions. Galactosyl iodides are intermediate in reactivity, providing the allyl glycoside in 3 h at room temperature, whereas glycosylation of fucosyl iodides occurs in less than 1 h under similar conditions. The scope and limitations of the reactions were demonstrated with a variety of acceptors, including an anomeric hydroxyl group, to give trehalose analogs. β-Selective glycosylation of glucosyl iodides, in the absence of C-2 participation, could be achieved by simply changing the solvent from benzene to acetonitrile. Copyright (C) 1999 Elsevier Science Ltd.
