202464-96-8Relevant articles and documents
Synthesis of α-l-rhamnosyl ceramide and evaluation of its binding with anti-rhamnose antibodies
Long, David E.,Karmakar, Partha,Wall, Katherine A.,Sucheck, Steven J.
, p. 5279 - 5289 (2014/12/11)
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.
Synthesis of an orthogonally protected d-(+)-erythro-sphingosine
Gargano, Joseph M.,Lees, Watson J.
, p. 5845 - 5847 (2007/10/03)
The synthesis presented provides rapid access to an orthogonally protected d-(+)-erythro-sphingosine: 1-methoxymethyl, 2-azido, 3-benzoyl. After selective deprotection the resulting sphingosine derivative is suitable for coupling to a wide variety of saccharides or other molecules at either the 1- or 3-position.
