58438-08-7Relevant academic research and scientific papers
Mycobacterium tuberculosis β-gentiobiosyl diacylglycerides signal through the pattern recognition receptor Mincle: Total synthesis and structure activity relationships
Richardson, Mark B.,Torigoe, Shota,Yamasaki, Sho,Williams, Spencer J.
supporting information, p. 15027 - 15030 (2015/10/12)
Mycobacterium tuberculosis H37Ra produces a range of immunogenic β-gentiobiosyl diacylglycerides. We report the total synthesis of several candidate structures and show that these compounds signal weakly through mouse, but not human, Mincle. Structure-activity relationships reveal a striking dependence upon acyl chain length for gentiobiosyl diacylglyceride signalling through Mincle. Significantly, a truncated β-glucosyl diglyceride was shown to provide potent signalling through both human and mouse Mincle and could activate murine bone marrow derived dendritic cells.
Synthesis of N-oxyamide-linked neoglycolipids
Chen, Na,Xie, Juan
, p. 10716 - 10721 (2015/02/19)
N-Oxyamide-containing compounds have shown improved metabolic stability and interesting secondary structures due to the good hydrogen bond-donating property of N-oxyamide. β-Glucolipids linked by the N-oxyamide bond have been successfully synthesized as novel mimics of glycoglycerolipids and glycosphingolipids.
A hydrophobic disordered peptide spontaneously anchors a covalently bound RNA hairpin to giant lipidic vesicles
Isaad, Alexandra Le Chevalier,Carrara, Paolo,Stano, Pasquale,Krishnakumar, Kollappillil S.,Lafont, Dominique,Zamboulis, Alexandra,Buchet, Rene,Bouchu, Denis,Albrieux, Florian,Strazewski, Peter
, p. 6363 - 6373 (2014/08/18)
The attraction of nucleic acids to lipidic compartments is the first step for carriers of potentially inheritable information to self-organise in functionalised synthetic cells. Confocal fluorescence imaging shows that a synthetic amphiphilic peptidyl RNA molecule spontaneously accumulates at the outer bilayer membranes of phospho- and glycolipidic giant vesicles. Cooperatively attractive interactions of -3.4 to -4.0 kcal mol-1 between a random coil hydrophobic peptide and lipid membranes can thus pilot lipophobic RNA to its compartmentation. The separation of mixed lipid phases in the membranes further enhances the local concentration of anchored RNA. the Partner Organisations 2014.
Synthesis and mesogenic properties of glycosyl diacylglycerols.
von Minden,Morr,Milkereit,Heinz,Vill
, p. 55 - 80 (2007/10/03)
We synthesised glycosyl diacylglycerols bearing unsaturated or chiral methyl branched fatty acid chains. The thermotropism was measured with polarising microscopy and additionally the lyotropism with the contact preparation method. The synthesised compoun
SYNTHESIS OF PHOSPHATIDYL-β-GLUCOSYL GLYCEROL CONTAINING A DIOLEOLYL DIGLYCERIDE MOIETY. APPLICATION OF THE TETRAISOPROPYLDISILOXANE-1,3-DIYL (TIPS) PROTECTING GROUP IN SUGAR CHEMISTRY. PART IV
Boeckel, C. A. A. van,Visser, G. M.,Boom, J. H. van
, p. 4557 - 4566 (2007/10/02)
The preparation of phosphatidyl-β-glucosyl diglyceride 12c is described.The synthesis of glycophospholipid 12c was accomplished by using: (a) the levulinoyl group for the temporary protection of the glucose hydroxyl functions of 6b, which could then be converted into the dioleoyl substituted derivative 7c; (b) the tetraisopropyldisiloxane-1,3-diyl (TIPS) group to protect the 3'- and 4'-hydroxyl groups of 7c, in a two step procedure, to afford compound 8; (c) a 2,4-dichlorophenyl protected phosphatidic acid derivative 11.Compound 11 could be selectively coupled to the primary hydroxyl function of 8 to afford the fully protected glycophospholipid 12a.Finally, removal of the 2,4-dichlorophenyl and TIPS protecting groups from 12a was performed with syn-4-nitrobenzaldoximate and fluoride ions, respectively, to afford glycophospholipid 12c.
SEPARATION OF RACEMATES OF 1,2-DISUBSTITUTED DERIVATIVES OF GLYCEROL INTO ANTIPODES
Andguladze, M. K.,Kaplun, A. P.,Kulish, M. A.,Shvets, V. I.
, p. 846 - 851 (2007/10/02)
1,2-Di-O-Benzyl-rac-glycerol (or 1-stearoyl-2-O-benzyl-rac-glycerol) was glycocylated with acetobromoglucose or mannose tert-butyl orthoacetate.The chromatographic chasracteristics of the synthesized 1,2-trans-glycosides and of the glycosides obtained by
LILIOSIDE C, A GLYCEROL GLUCOSIDE FROM LILIUM LANCIFOLIUM
Kaneda, Miyuki,Mizutani, Kiyoyasu,Tanaka, Keiko
, p. 891 - 894 (2007/10/02)
A new glycerol glucoside, lilioside C, has been isolated from the leaves and stems of Lilium lancifolium.Its structure including the configuration of the aglycone moiety has been elucidated by chemical and spectroscopic means and by its synthesis.Key Word Index - Lilium lancifolium; Liliaceae; tiger lily; glycerol glucoside; 3-O-β-D-glucopyranosyl-sn-glycerol; lilioside C; stereochemistry; synthesis.
SYNTHESIS OF A TEICHOIC ACID FRAGMENT OF BACILLUS VAR. NIGER W.M. BY A PHOSPHOTRIESTER APPROACH
van Boeckel, C.A.A.,Visser, G. M.,Hermans, J.P.G.,van Boom, J.H.
, p. 4743 - 4746 (2007/10/02)
Three properly-protected derivatives, one non-terminal and two terminal units, of 3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-sn-glycerol have been joined together by two interglyceridic phosphotriester linkages to afford, after removal of all pro
