Chemical Synthesis of d-glycero-d-manno-Heptose 1,7-Bisphosphate and Evaluation of Its Ability to Modulate NF-κB Activation
作者： Shinsuke Inuki , Toshihiko Aiba , Shota Kawakami , Taishin Akiyama , Jun-ichiro Inoue
DOI: 10.1021/ACS.ORGLETT.7B01158
关键词:
摘要: 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 chemical synthesis of α- β-anomers, which highlights C-7 carbon homologation via Corey–Chaykovsky reaction, introduction phosphate group at anomeric position using Mitsunobu reaction. Furthermore, NF-κB reporter assaying revealed activates signaling pathway.
acs.org
elsevier.com
sci-hub.se 参考文章(34)
Oyo Mitsunobu, The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products Synthesis. ,vol. 1981, pp. 1- 28 ,(1981) , 10.1055/S-1981-29317
Daniel A. Ryan, David Y. Gin, Xiangming Zhu, Richard R. Schmidt, Glycoside Synthesis from 1‐Oxygen Substituted Glycosyl Donors: Sections 3.1 and 3.2 John Wiley & Sons, Ltd. pp. 95- 185 ,(2008) , 10.1002/9783527621644.CH3A
R. G. Gaudet, A. Sintsova, C. M. Buckwalter, N. Leung, A. Cochrane, J. Li, A. D. Cox, J. Moffat, S. D. Gray-Owen, Cytosolic detection of the bacterial metabolite HBP activates TIFA-dependent innate immunity Science. ,vol. 348, pp. 1251- 1255 ,(2015) , 10.1126/SCIENCE.AAA4921
Christian Stanetty, Ian R. Baxendale, Large-Scale Synthesis of Crystalline 1,2,3,4,6,7-Hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose† European Journal of Organic Chemistry. ,vol. 2015, pp. 2718- 2726 ,(2015) , 10.1002/EJOC.201500024
Krzysztof Dziewiszek, Anna Banaszek, Aleksander Zamojski, The synthesis of the heptose region of the gram-negative bacterial core oligosaccharides Tetrahedron Letters. ,vol. 28, pp. 1569- 1572 ,(1987) , 10.1016/S0040-4039(01)81044-3
John S. Brimacombe, Abul K.M.S. Kabir, A synthesis of l-galacto-d-galacto-decose☆ Carbohydrate Research. ,vol. 152, pp. 335- 338 ,(1986) , 10.1016/S0008-6215(00)90317-3
Alla Zamyatina, Sabine Gronow, Michael Puchberger, Andrea Graziani, Andreas Hofinger, Paul Kosma, Efficient chemical synthesis of both anomers of ADP l-glycero- and d-glycero-d-manno-heptopyranose Carbohydrate Research. ,vol. 338, pp. 2571- 2589 ,(2003) , 10.1016/S0008-6215(03)00319-7
David Crich, Vadim Dudkin, Efficient, Diastereoselective Chemical Synthesis of a β-Mannopyranosyl Phosphoisoprenoid Organic Letters. ,vol. 2, pp. 3941- 3943 ,(2000) , 10.1021/OL006725P
Ruslan Medzhitov, Approaching the Asymptote: 20 Years Later Immunity. ,vol. 30, pp. 766- 775 ,(2009) , 10.1016/J.IMMUNI.2009.06.004
Matthew J. McKay, Hien M. Nguyen, Recent Advances in Transition Metal-Catalyzed Glycosylation ACS Catalysis. ,vol. 2, pp. 1563- 1595 ,(2012) , 10.1021/CS3002513