1224436-75-2Relevant academic research and scientific papers
Total Synthesis of Marine Glycosphingolipid Vesparioside B
Gao, Peng-Cheng,Zhu, San-Yong,Cao, Hui,Yang, Jin-Song
, p. 1684 - 1688 (2016)
The first total synthesis of a major component of marine glycolipid vesparioside B (Scheme 1, 1, R1 = n-C22H45, R2 = n-C14H29) has been accomplished through a convergent [4 + 3] coupling strategy. Key steps included stereoselective installment of a set of challenging 1,2-cis-glycoside bonds. A 2-quinolinecarbonyl-assisted α-galactosylation and a novel β-arabinosylation were developed, respectively, to synthesize the α-galactofuranosidic and the β-arabinopyranosidic linkages. Furthermore, a 4,6-O-benzylidene-controlled α-galactopyranosylation reaction allowed the efficient connection of the left tetrasaccharide donor 2 with the right disaccharide lipid acceptor 3, hence leading to the total synthesis of 1.
Total Synthesis of Phospholipomannan of Candida albicans
Ali, Asif,Gannedi, Veeranjaneyulu,Singh, Parvinder Pal,Vishwakarma, Ram A.
, p. 7757 - 7771 (2020/07/25)
First, total synthesis of the cell surface phospholipomannan anchor [β-Manp-(1 → 2)-β-Manp]n-(1 → 2)-β-Manp-(1 → 2)-α-Manp-1 → P-(O → 6)-α-Manp-(1 → 2)-Inositol-1-P-(O → 1)-phytoceramide of Candida albicans is reported. The target phospholipomannan (PLM) anchor poses synthetic challenges such as the unusual kinetically controlled (1 → 2)-β-oligomannan domain, anomeric phosphodiester, and unique phytoceramide lipid tail linked to the glycan through a phosphate group. The synthesis of PLM anchor was accomplished using a convergent block synthetic approach using three main appropriately protected building blocks: (1 → 2)-β-tetramannan repeats, pseudodisaccharide, and phytoceramide-1-H-phosphonate. The most challenging (1 → 2)-β-tetramannan domain was synthesized in one pot using the preactivation method. The phytoceramide-1-H-phosphonate was synthesized through an enantioselective A3 three-component coupling reaction. Finally, the phytoceramide-1-H-phosphonate moiety was coupled with pseudodisaccharide followed by deacetylation to produce the acceptor, which on subsequent coupling with tetramannosyl-H-phosphonate provided the fully protected PLM anchor. Final deprotection was successfully achieved by Pearlman's hydrogenation.
INKT CELL MODULATORS AND METHODS OF USING THE SAME
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Paragraph 0068; 00156, (2013/06/27)
Disclosed herein are α-galactosylceramide (α-GalCer) analogs and compositions thereof, methods of activating invariant Natural Killer T (iNKT) cells using said analogs, methods of treating diseases by activating iNKT cells using said analogs, and combinat
Synthesis of a novel α-galactosyl ceramide haptenated-lipid antigen, a useful tool in demonstrating the involvement of i NKT cells in the production of antilipid antibodies
Veerapen, Natacha,Leadbetter, Elizabeth A.,Brenner, Michael B.,Cox, Liam R.,Besra, Gurdyal S.
scheme or table, p. 741 - 747 (2011/02/25)
A new haptenated derivative of α-galactosyl ceramide (α-GalCer) has been synthesized to assist in the study of the mechanism of T cell help for the production of B cell antibodies. Our synthetic route provides access to an amine intermediate which can eas
