132842-33-2

Upstream product

• 1161750-38-4 C₃₈H₅₆O₃ 
• 126960-18-7 (R)-1-(Benzyloxy)-4-tetracosyn-2-ol 
• 61847-81-2 1-Heneicosyne 
• 1161750-39-5 C₃₁H₅₂O₃ 
• 132842-32-1 Benzoic acid (R)-1-((S)-1,2-dihydroxy-ethyl)-tricosyl ester 

Downstream Products

• 1161750-41-9 (2S,3R,4E)-2-[(R)-2-(benzoyloxy)tetracosanoylamino]-15-methylhexadec-4-ene-1,3-diol 

Relevant academic research and scientific papers

Total Synthesis of the Echinodermatous Ganglioside LLG-3 Possessing the Biological Function of Promoting the Neurite Outgrowth

A total synthesis of echinodermatous ganglioside LLG-3 with neuritogenic activity was accomplished by a convergent strategy. The synthesis of 2-hydroxyethyl 8-O-Me-α-sialoside 2 was started from the phenyl 7,8-di-O-Pico-thiosialoside 5, which can be chemoselectively removed the picoloyl group, and then the methyl group in 8-O-MeNeu5Ac moiety was chemoselectively prepared using TMSCHN2/FeCl3. For preparation of the terminal disialic unit, oxidative amidation was initially utilized by our group to efficiently construct the α(2,11) linkage of 8-O-Me-Neu5Acα(2,11)Neu5Gc. Herein, we also demonstrate that the synthesized ganglioside LLG-3 exhibited the neuritogenic activity toward the primary cortical neurons and that biological activity is superior to that of ganglioside DSG-A.

Influence of Gb3 glycosphingolipids differing in their fatty acid chain on the phase behaviour of solid supported membranes: Chemical syntheses and impact of Shiga toxin binding

The Shiga toxin B subunit (STxB), which is involved in cell membrane attachment and trafficking of Shiga holotoxin, binds specifically to the glycosphingolipid Gb3. In biological membranes, Gb3 glycosphingolipids differ in their fatty acid composition and there is strong evidence that the fatty acid alters the binding behaviour of STxB as well as the intracellular routing of the Shiga toxin/Gb3 complex. To analyse the binding of STxB to different Gb3s, we chemically synthesized saturated, unsaturated, α-hydroxylated Gb3s and a combination thereof, all based on a C24-fatty acid chain starting from monosaccharide building blocks, sphingosine and the respective fatty acids. These chemically well-defined Gb3s were inserted into solid supported phase-separated lipid bilayers composed of DOPC/sphingomyelin/cholesterol as a simple mimetic of the outer leaflet of animal cell membranes. By fluorescence- and atomic force microscopy the phase behaviour of the bilayer as well as the lateral organization of bound STxB were analysed. The fatty acid of Gb 3 significantly alters the ratio between the ordered and disordered phase and induces a third intermediate phase in the presence of unsaturated Gb3. The lateral organization of STxB on the membranes varies significantly. While STxB attached to membranes with Gb3s with saturated fatty acids forms protein clusters, it is more homogeneously bound to membranes containing unsaturated Gb3s. Large interphase lipid redistribution is observed for α-hydroxylated Gb3 doped membranes. Our results clearly demonstrate that the fatty acid of Gb3 strongly influences the lateral organization of STxB on the membrane and impacts the overall membrane organization of phase-separated lipid membranes. the Partner Organisations 2014.

A first total synthesis of ganglioside HLG-2

A first synthesis of the neuri-tegenic ganglioside HLG-2, which was identified in extracts of the sea cucumber Holothuria leucospilota, is described. The characteristic sequence of the trisaccharide part, α-N-glycolylsial-yl-(2,4)-& α-N-acetylsialyl-(2,6)-glucoside, was efficiently assembled by coupling of a highly active N-2,2,2-trichloro- ethoxycarbonyl (Troc)-protected sialyl donor and a 1,5-lactamized sialyl ac- ceptor with high stereoselectivity. The corresponding trisaccharyl imidate donor was directly glycosidated with the primary hydroxyl group of the ceramide part, producing protected HLG-2 in relatively high yield, global deprotection of which furnished ganglioside HLG-2 in highly pure form.

Synthesis of Chiral Long-chain α-Hydroxy Acids from L-Ascorbic Acid. Useful Components for the Synthesis of Cerebrosides

Nucleophilic ring opening of chiral epoxy diols, derived from L-ascorbic acid, with 2-lithio-1,3-dithianes allowed preparation of long-chain (R)- and (S)-α-hydroxy acids of high optical purity.