<?xml version="1.0" encoding="UTF-8"?><xml><records><record><source-app name="Biblio" version="6.x">Drupal-Biblio</source-app><ref-type>17</ref-type><contributors><authors><author><style face="normal" font="default" size="100%">Ainge, G.D.</style></author><author><style face="normal" font="default" size="100%">Compton, B.J.</style></author><author><style face="normal" font="default" size="100%">Hayman, C.M.</style></author><author><style face="normal" font="default" size="100%">Martin, W.J.</style></author><author><style face="normal" font="default" size="100%">Toms, S.M.</style></author><author><style face="normal" font="default" size="100%">Larsen, D.S.</style></author><author><style face="normal" font="default" size="100%">Harper, J.L.</style></author><author><style face="normal" font="default" size="100%">Painter, G.F.</style></author></authors><translated-authors><author><style face="normal" font="default" size="100%">Carbohydrate Chemistry</style></author></translated-authors></contributors><titles><title><style face="normal" font="default" size="100%">Chemical synthesis and immunosuppressive activity of dipalmitoyl phosphatidylinositol hexamannoside</style></title><secondary-title><style face="normal" font="default" size="100%">Journal of Organic Chemistry</style></secondary-title></titles><keywords><keyword><style  face="normal" font="default" size="100%">article</style></keyword><keyword><style  face="normal" font="default" size="100%">CD8+ T lymphocyte</style></keyword><keyword><style  face="normal" font="default" size="100%">Chemical modification</style></keyword><keyword><style  face="normal" font="default" size="100%">chemical structure</style></keyword><keyword><style  face="normal" font="default" size="100%">Chemical synthesis</style></keyword><keyword><style  face="normal" font="default" size="100%">chromatography</style></keyword><keyword><style  face="normal" font="default" size="100%">Deacylation</style></keyword><keyword><style  face="normal" font="default" size="100%">dendritic cell</style></keyword><keyword><style  face="normal" font="default" size="100%">dipalmitoylphosphatidylinositol hexamannoside</style></keyword><keyword><style  face="normal" font="default" size="100%">esterification</style></keyword><keyword><style  face="normal" font="default" size="100%">Glycosylation</style></keyword><keyword><style  face="normal" font="default" size="100%">H NMR spectra</style></keyword><keyword><style  face="normal" font="default" size="100%">high performance liquid chromatography</style></keyword><keyword><style  face="normal" font="default" size="100%">human</style></keyword><keyword><style  face="normal" font="default" size="100%">human cell</style></keyword><keyword><style  face="normal" font="default" size="100%">immunomodulating agent</style></keyword><keyword><style  face="normal" font="default" size="100%">immunomodulation</style></keyword><keyword><style  face="normal" font="default" size="100%">Mixed lymphocyte reaction</style></keyword><keyword><style  face="normal" font="default" size="100%">Mycobacterium</style></keyword><keyword><style  face="normal" font="default" size="100%">nonhuman</style></keyword><keyword><style  face="normal" font="default" size="100%">nuclear magnetic resonance spectroscopy</style></keyword><keyword><style  face="normal" font="default" size="100%">phosphatidylinositol</style></keyword><keyword><style  face="normal" font="default" size="100%">proton nuclear magnetic resonance</style></keyword><keyword><style  face="normal" font="default" size="100%">Reverse phase chromatography</style></keyword><keyword><style  face="normal" font="default" size="100%">Spectroscopic analysis</style></keyword><keyword><style  face="normal" font="default" size="100%">Spectroscopic method</style></keyword><keyword><style  face="normal" font="default" size="100%">Sugars</style></keyword><keyword><style  face="normal" font="default" size="100%">synthesis</style></keyword><keyword><style  face="normal" font="default" size="100%">Synthesis (chemical)</style></keyword><keyword><style  face="normal" font="default" size="100%">Synthetic protocols</style></keyword><keyword><style  face="normal" font="default" size="100%">T cells</style></keyword><keyword><style  face="normal" font="default" size="100%">unclassified drug</style></keyword></keywords><dates><year><style  face="normal" font="default" size="100%">2011</style></year></dates><urls><web-urls><url><style face="normal" font="default" size="100%">http://www.scopus.com/inward/record.url?eid=2-s2.0-79958837488&partnerID=40&md5=9d0be249bce03475f7210fb73213d868</style></url></web-urls></urls><volume><style face="normal" font="default" size="100%">76</style></volume><pages><style face="normal" font="default" size="100%">4941-4951</style></pages><language><style face="normal" font="default" size="100%">eng</style></language><abstract><style face="normal" font="default" size="100%">Phosphatidylinositol mannosides (PIMs) isolated from mycobacteria have been identified as an important class of phosphoglycolipids with significant immune-modulating properties. We present here the synthesis of dipalmitoyl phosphatidylinositol hexamannoside (PIM6) 1 and the first reported functional biology of a synthetic PIM6. Key steps in the synthetic protocol included the selective glycosylation of an inositol 2,6-diol with a suitably protected mannosyl donor and construction of the glycan core utilizing a [3 + 4] thio-glycosylation strategy. The target 1 was purified by reverse phase chromatography and characterized by standard spectroscopic methods, HPLC, and chemical modification by deacylation to dPIM6. The 1H NMR spectrum of synthetic dPIM6 obtained from 1 matched that of dPIM6 obtained from nature. PIM6 (1) exhibited dendritic cell-dependent suppression of CD8+ T cell expansion in a human mixed lymphocyte reaction consistent with the well established immunosuppressive activity of whole mycobacteria. © 2011 American Chemical Society.</style></abstract></record></records></xml>
