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• W2065683541 abstract "An α- l -rhamnosyl ceramide ( 1 , α- l -RhaCer) has been prepared that was recognized by anti- l -rhamnose (anti-Rha) antibodies. During these studies we explored the use of an α- l -rhamnosyl thioglycoside and a trichloroacetimidate as a glycosyl donors. Subsequently, the acceptors desired for glycosylation, 3- O -benzoylazidosphingosine or 3- O -alloxycarbonylsphingosine, were prepared from d -xylose. The thioglycoside donor, 2,3,4-tri- O -acetyl-1-(4-tolyl)thio-α- l -rhamnopyranoside, and the trichloroacetimidate donor, 2,3,4-tri- O -acetyl-1-(2,2,2-trichloroethanimidate)-α- l -rhamnopyranoside, were synthesized in 50% and 78% yield overall, respectively. The synthesis of the glycosylation acceptor employed an addition–fragmentation olefination that was successfully carried out in 53% yield. With the successful synthesis of key intermediates, α- l -RhaCer ( 1 ) was prepared without any insurmountable obstacles. Anti-Rha antibodies were prepared in BALB/c mice by immunizing them with rhamnose-ovalbumin (Rha-Ova) with Sigma Adjuvant System (SAS) and the anti- l -Rha antibodies were isolated from the blood sera. Liposomes and EL4 tumor cells were used as model systems to demonstrate the ability of 1 to insert into a lipid bilayer. The interaction of the liposomes or the EL4 cells with α- l -RhaCer ( 1 ) and anti-Rha antibodies were investigated by fluorescence microscopy and flow cytometry, respectively, to confirm the ability of glycolipid 1 to be displayed on the tumor cell surface as well as the ability to be recognized by anti-Rha antibodies." @default.
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• W2065683541 date "2014-10-01" @default.
• W2065683541 modified "2023-09-26" @default.
• W2065683541 title "Synthesis of α-l-rhamnosyl ceramide and evaluation of its binding with anti-rhamnose antibodies" @default.
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• W2065683541 doi "https://doi.org/10.1016/j.bmc.2014.08.002" @default.
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