Preparation of a Lipid A Derivative That Contains a 27-Hydroxyoctacosanoic Acid Moiety
作者： Balaji Santhanam , Geert-Jan Boons
DOI: 10.1021/OL048746F
关键词: Tumor necrosis factor alpha 、 Stereochemistry 、 Reaction step 、 Lipid A 、 Rhizobium 、 27-hydroxyoctacosanoic acid 、 Moiety 、 Metathesis 、 Chemistry
摘要: A general synthetic strategy for long-chain ω-1 hydroxy fatty acids has been developed, which employs as a key reaction step cross metathesis between ω-unsaturated ester and 3-butene-2-ol. The resulting lipids were used the preparation of lipid derivatives Rhizobium sin-1, have ability to inhibit E. coli LPS-dependent synthesis tumor necrosis factor by human monocytes.
acs.org
sci-hub.se 参考文章(19)
E. T. Rietschel, H. Brade, O. Holst, L. Brade, S. Müller-Loennies, U. Mamat, U. Zähringer, F. Beckmann, U. Seydel, K. Brandenburg, A. J. Ulmer, T. Mattern, H. Heine, J. Schletter, H. Loppnow, U. Schönbeck, H.-D. Flad, S. Hauschildt, U. F. Schade, F. Di Padova, S. Kusumoto, R. R. Schumann, Bacterial Endotoxin: Chemical Constitution, Biological Recognition, Host Response, and Immunological Detoxification Current Topics in Microbiology and Immunology. ,vol. 216, pp. 39- 81 ,(1996) , 10.1007/978-3-642-80186-0_3
K D Noel, K A Vandenbosch, B Kulpaca, Mutations in Rhizobium phaseoli that lead to arrested development of infection threads. Journal of Bacteriology. ,vol. 168, pp. 1392- 1401 ,(1986) , 10.1128/JB.168.3.1392-1401.1986
Masato Oikawa, Shoichi Kusumoto, On a practical synthesis of β-hydroxy fatty acid derivatives Tetrahedron-asymmetry. ,vol. 6, pp. 961- 966 ,(1995) , 10.1016/0957-4166(95)00106-Y
G.H. Veeneman, S.H. van Leeuwen, J.H. van Boom, Iodonium ion promoted reactions at the anomeric centre. II An efficient thioglycoside mediated approach toward the formation of 1,2-trans linked glycosides and glycosidic esters Tetrahedron Letters. ,vol. 31, pp. 1331- 1334 ,(1990) , 10.1016/S0040-4039(00)88799-7
Stanley B. Mirviss, Synthesis of .omega.-unsaturated acids Journal of Organic Chemistry. ,vol. 54, pp. 1948- 1951 ,(1989) , 10.1021/JO00269A038
Elmar L. Kannenberg, Russell W. Carlson, Lipid A and O-chain modifications cause Rhizobium lipopolysaccharides to become hydrophobic during bacteroid development. Molecular Microbiology. ,vol. 39, pp. 379- 392 ,(2001) , 10.1046/J.1365-2958.2001.02225.X
Silke Schneider, Marcel G. Wubbolts, Dominique Sanglard, Bernard Witholt, Production of chiral hydroxy long chain fatty acids by whole cell biocatalysis of pentadecanoic acid with an E. coli recombinant containing cytochrome P450BM-3 monooxygenase Tetrahedron-asymmetry. ,vol. 9, pp. 2832- 2844 ,(1998) , 10.1016/S0957-4166(98)00283-3
Michel L. Vandenplas, Russell W. Carlson, Benjamin S. Jeyaretnam, Brian McNeill, Michelle H. Barton, Natalie Norton, Thomas F. Murray, James N. Moore, RhizobiumSin-1 Lipopolysaccharide (LPS) Prevents Enteric LPS-induced Cytokine Production Journal of Biological Chemistry. ,vol. 277, pp. 41811- 41816 ,(2002) , 10.1074/JBC.M205252200
Benjamin Jeyaretnam, John Glushka, V. S. Kumar Kolli, Russell W. Carlson, Characterization of a Novel Lipid-A fromRhizobium Species Sin-1 A UNIQUE LIPID-A STRUCTURE THAT IS DEVOID OF PHOSPHATE AND HAS A GLYCOSYL BACKBONE CONSISTING OF GLUCOSAMINE AND 2-AMINOGLUCONIC ACID Journal of Biological Chemistry. ,vol. 277, pp. 41802- 41810 ,(2002) , 10.1074/JBC.M112140200
Alexei V. Demchenko, Margreet A. Wolfert, Balaji Santhanam, James N. Moore, Geert-Jan Boons, Synthesis and biological evaluation of Rhizobium sin-1 lipid A derivatives. Journal of the American Chemical Society. ,vol. 125, pp. 6103- 6112 ,(2003) , 10.1021/JA029316S