000059753 001__ 59753
000059753 005__ 20180317092302.0
000059753 0247_ $$2doi$$a10.1002/hlca.200490096
000059753 022__ $$a0018-019X
000059753 02470 $$2DAR$$a5291
000059753 02470 $$2ISI$$a000222297200002
000059753 037__ $$aARTICLE
000059753 245__ $$aNew nonhydrolyzable mimetics of sialyl Lewis x and their binding affinity to P-selectin
000059753 260__ $$c2004
000059753 269__ $$a2004
000059753 336__ $$aJournal Articles
000059753 500__ $$aEcole Polytech Fed Lausanne, BCH, Inst Sci & Ingn Chim, CH-1015 Lausanne, Switzerland. CHU Vaudois, Inst Hematol, CH-1011 Lausanne, Switzerland.
000059753 520__ $$aWittig olefination of (2S,3R,5S,6R)-5-(acetyloxy)-tetrahydro-6-[(methoxymethoxy)methyl]-3-(phe nylthio)2H-pyran-2-acetaldehyde ((+)-10) with {2-[(2S,3R,4R,5R,6S)-tetrahydro-3,4,5-tris(methoxymethoxy)-6-methyl-2H-p yran-2-yl]ethyl}triphenylphosphonium iodide ((-)-11) gave a (Z)-alkene derivative (+)-12 that was converted into (alphaR,2R,3S,4R,5R,6S)-tetrahydro-alpha,3-dihydroxy-2-(hydroxymethyl)-5 -(phenylthio)-6-{(2Z)-4-[(2S,3S,4R,5S,6S)-tetrahydro-3,4,5-trihydroxy-6- methyl-2H-pyran-2-yl]but-2-enyl}2H-pyran-4-acetic acid (8), (alphaR,2R,3S,4R,6S)-tetrahydro-alpha,3-dihydroxy-2-(hydroxymethyl)-6-{4 -[(2S,3S,4R,5S,6S)-tetrahydro-3,4,5-trihydroxy-6-methyl-2H-pyran-2-yl]bu tyl}-2H-pyran-4-acetic acid (9), and simpler analogues without the hydroxyacetic side chain such as (2S,3S,4R,5S,6S)-tetrahydro-6-methyl-2-{(2Z)-4-[(2S,3R,5S,6R)-tetrahydro -5-hydroxy-6-(hydroxymethyl)-3-(phenylthio)-2H-pyran-2-yl]but-2-enyl}-2H -pyran-3,4,5-triol (30), (2S,3S,4R,5S,6S)-tetrahydro-6-methyl-2-{[(2S,5S,6R)-tetrahydro-5-hydroxy -6-(hydroxymethyl)-2H-pyran-2-yl]butyl}-2H-pyran-3,4,5-triol ((-)-41) and (2S,3S,4R,5S,6S)-tetrahydro-6-methyl-2-{(2Z/E))-4-[(2R,5S,6R)-tetrahydro -5-hydroxy-6-(hydroxymethyl)-2H-pyran-2-yl]but-2-enyl}-2H-pyran-3,4,5-tr iol (43). The key intermediates (+)-10 and (-)-11 were derived from isolevoglucosenone and from L-fucose, respectively. The following IC50 values were measured in a ELISA test for the affinities of sialyl Lewis x tetrasaccharide, 8, 9. 30, (-)-41, and 43 toward P-selectin: 0.7, 2.5-2.8, 7.3-8.0, 5.3-5.9, 5.0-5.2, and 3.4-4.1 mM, respectively.
000059753 6531_ $$aBiological evaluation
000059753 6531_ $$amolecular-basis
000059753 6531_ $$acell-adhesion
000059753 6531_ $$ainhibitors
000059753 6531_ $$adesign
000059753 6531_ $$amimics
000059753 6531_ $$adisaccharides
000059753 6531_ $$aantagonists
000059753 6531_ $$areduction
000059753 6531_ $$aanalogs
000059753 700__ $$0241592$$aCarrel, F.$$g148234
000059753 700__ $$aGiraud, S.
000059753 700__ $$aSpertini, O.
000059753 700__ $$0240222$$aVogel, P.$$g123681
000059753 773__ $$j87$$k5$$q1048-1070$$tHelvetica Chimica Acta
000059753 909CO $$ooai:infoscience.tind.io:59753$$particle$$pSB
000059753 909C0 $$0252076$$pLGSA$$xU10111
000059753 937__ $$aLGSA-ARTICLE-2004-009
000059753 970__ $$aISI:000222297200002/LGSA
000059753 973__ $$aEPFL$$rREVIEWED$$sPUBLISHED
000059753 980__ $$aARTICLE