157639-67-3Relevant articles and documents
Cesium trifluoroacetate or silver oxide mediated acyl migration for the construction of disaccharide building blocks
Deng, Shenglou,Chang, Cheng-Wei Tom
, p. 756 - 760 (2006)
A convenient method for the selective differentiation of the 2-OH and 3-OH of pyranosides, based on the CsO2CCF3- or Ag 2O-mediated acyl migration, has been established. The 2-OH and 3-OH can be sequentially glycosylated b
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 5a-Carba-&β-D-glycosylceramide Analogs Linked by Imino, Ether and Sulfide Bridges
Tsunoda, Hidetoshi,Ogawa, Seiichiro
, p. 267 - 278 (2007/10/02)
Carbocyclic analogs of glycoceramides, (2S,3R,4E)-1-(5a-carba-β-D-glycopyranosyl)-2-(hexadecanoylamino)-4-octadecen-3-ols E-3 - E-6, linked by imino, ether and sulfide bridges, were synthesized by coupling of aziridines, as the sphingosine precursors, wit
