103348-49-8Relevant articles and documents
A simple and low cost synthesis of D-erythro-sphingosine and D-erythro-azidosphingosine from D-ribo-phytosphingosine: Glycosphingolipid precursors
Van Den Berg, Richard J.B.H.N.,Korevaar, Cornelis G.N.,Van Der Marel, Gijsbert A.,Overkleeft, Herman S.,Van Boom, Jacques H.
, p. 8409 - 8412 (2002)
D-erythro-Sphingosine (1) and D-erythro-2-azidosphingosine (2) are both prepared from commercially available and cheap D-ribo-phytosphingosine (3) in a yield of 58% and 70%, respectively. A key transformation in the synthesis of D-erythro-sphingosine (1) is the palladium catalyzed regiospecific reduction of the Z-enol triflate 9. A crucial step in the synthesis of azidosphingosine 2 comprises a regio- and stereoselective in situ trans-elimination of the 4-O-triflate of azidophytosphingosine 13.
CD1a-binding glycosphingolipids stimulating human autoreactive T-cells: Synthesis of a family of sulfatides differing in the acyl chain moiety
Compostella, Federica,Franchini, Laura,De Libero, Gennaro,Palmisano, Giovanni,Ronchetti, Fiamma,Panza, Luigi
, p. 8703 - 8708 (2002)
Native sulfatide (a mixture of 3-sulfated β-D-galactopyranosylceramides with different fatty acids at the ceramide moiety) is an antigen presented by CD1a proteins. Herein the preparation of four sulfatides, which are constituents of the natural mixture a
Synthesis of Gb3 Glycosphingolipids with Labeled Head Groups: Distribution in Phase-Separated Giant Unilamellar Vesicles
Sibold, Jeremias,Kettelhoit, Katharina,Vuong, Loan,Liu, Fangyuan,Werz, Daniel B.,Steinem, Claudia
supporting information, p. 17805 - 17813 (2019/11/13)
The receptor lipid Gb3 is responsible for the specific internalization of Shiga toxin (STx) into cells. The head group of Gb3 defines the specificity of STx binding, and the backbone with different fatty acids is expected to influence its localization within membranes impacting membrane organization and protein internalization. To investigate this influence, a set of Gb3 glycosphingolipids labeled with a BODIPY fluorophore attached to the head group was synthesized. C24 fatty acids, saturated, unsaturated, α-hydroxylated derivatives, and a combination thereof, were attached to the sphingosine backbone. The synthetic Gb3 glycosphingolipids were reconstituted into coexisting liquid-ordered (lo)/liquid-disordered (ld) giant unilamellar vesicles (GUVs), and STx binding was verified by fluorescence microscopy. Gb3 with the C24:0 fatty acid partitioned mostly in the lo phase, while the unsaturated C24:1 fatty acid distributes more into the ld phase. The α-hydroxylation does not influence its partitioning.
One-pot syntheses of immunostimulatory glycolipids
Schombs, Matthew,Park, Francine E.,Du, Wenjun,Kulkarni, Suvarn S.,Gervay-Hague, Jacquelyn
scheme or table, p. 4891 - 4898 (2010/10/21)
(Figure presented) Glycolipids containing α-linked galactosyl and glucosyl moieties have been shown to possess unique immunostimulatory activity creating a need for access to diverse and anomerically pure sources of these compounds for immunological studies. To meet this demand, glycosyl iodides were enlisted in the synthesis of these biologically relevant glycoconjugates. In the first-generation protocol, per-O-benzyl galactosyl iodide was efficiently coupled with activated sphingosine acceptors, but fully functionalized ceramides were found to be unreactive. To overcome this obstacle, per-O-trimethylsilyl glycosyl iodides were investigated and shown to undergo highly efficient coupling with ceramide and glycerol ester acceptors. Contrary to what has been observed with other donors, we detected little difference between the reactivity of glucosyl and galactosyl iodides. The trimethylsilyl protecting groups play a dual role in activating the donor toward nucleophilic attack while at the same time providing transient protection: the silyl groups are readily removed upon methanolysis. All reactions proceeded with complete acceptor regioselectivity, eliminating the need for additional protecting group manipulations, and the desired α-anomers were formed exclusively. This three-step, one-pot synthetic platform provides rapid access to an important class of immunostimulatory molecules including the first reported synthesis of the glucosyl analogue of the bacterial antigen BbGL-II.
