67337-03-5

Usage

Uses

Used in Pharmaceutical Industry:
1,2-O-Dihexadecyl-sn-glycerol is used as a key component in the preparation of Toll-like Receptor-2 (TLR2) agonistic diacylthioglycerol lipopeptides. These lipopeptides are important for modulating the immune response and have potential applications in the development of vaccines and therapies for various diseases.
Used in Chemical Synthesis:
1,2-O-Dihexadecyl-sn-glycerol is utilized in the synthesis of phospholipid analogs, which are essential for the development and evaluation of phosphatidylinositol 4-kinase inhibitors. These inhibitors play a crucial role in understanding and targeting the molecular mechanisms involved in various cellular processes and diseases.

Upstream product

• 157999-06-9 2,3-Di-O-hexadecyl-sn-glycerol 1-(3'-nitrobenzenesulfonate) 
• 13071-57-3 (R)-((2,3-bis(hexadecyloxy)propoxy)methyl)benzene 
• 112-82-3 hexadecanyl bromide 
• 36653-82-4 1-Hexadecanol 
• 119879-73-1 3-O-Hexadecyl-sn-glycerol 1-(3'-nitrobenzenesulfonate) 

Downstream Products

• 34351-99-0 (2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R)-6-(2,3-Bis-hexadecyloxy-propoxy)-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 161003-27-6 Phosphoric acid (R)-2,3-bis-hexadecyloxy-propyl ester 4-(diphenoxy-phosphoryloxy)-cyclohexyl ester phenyl ester 
• 210221-82-2 (2'R)-2',3'-di-hexadecyloxypropyl-O-(4,6-benzylidene)-β-D-galactopyranoside 
• 210221-83-3 (2'R)-2',3'-di-hexadecyloxypropyl-O-<(4,6-benzylidene)-2,3-di-O-sulfonyl>-β-D-galactopyranoside 
• 1221430-17-6 (R)-2,3-bis(hexadecyloxy)propyl 4-methylbenzenesulfonate 
• 1337526-95-0 (4R,7S,10R,14R)-benzyl 10-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-carbamoyl-7-ethyl-14-(hexadecyloxy)-6,9-dioxo-16-oxa-12-thia-5,8-diazadotriacontan-1-oate 

Relevant academic research and scientific papers

Structure-activity relationships in toll-like receptor-2 agonistic diacylthioglycerol lipopeptides

The N-termini of bacterial lipoproteins are acylated with a (S)-(2,3-bisacyloxypropyl)cysteinyl residue. Lipopeptides derived from lipoproteins activate innate immune responses by engaging Toll-like receptor 2 (TLR2) and are highly immunostimulatory and yet without apparent toxicity in animal models. The lipopeptides may therefore be useful as potential immunotherapeutic agents. Previous structure-activity relationships in such lipopeptides have largely been obtained using murine cells, and it is now clear that significant species-specific differences exist between human and murine TLR responses. We have examined in detail the role of the highly conserved Cys residue as well as the geometry and stereochemistry of the Cys-Ser dipeptide unit. (R)-Diacylthioglycerol analogues are maximally active in reporter gene assays using human TLR2. The Cys-Ser dipeptide unit represents the minimal part-structure, but its stereochemistry was found not to be a critical determinant of activity. The thioether bridge between the diacyl and dipeptide units is crucial, and replacement by an oxoether bridge results in a dramatic decrease in activity.

ANALOGUES OF PHOSPHATIDYLINOSITOL MANNOSIDES

The invention relates to compounds which are immunomodulatory compounds and, in particular, can induce IL-12 secretion. The invention also relates to compositions containing the compounds, precursors, and prodrugs of these compounds, use of these compounds as adjuvants in combination with vaccines, and use of these compounds for treatment of diseases or conditions relating to infection, atopic disorders, or cancer.

Synthesis of the sialyl Lewis X epitope attached to glycolipids with different core structures and their selectin-binding characteristics in a dynamic test system

Sialyl Lewis X (sLe(X))/selectin-mediated leukocyte rolling along endothelial cells has recently gained wide interest. In this paper the influence of the spacer length of laterally clustered neoglycolipids 1a-d on cell rolling in a dynamic test system is

Short synthesis of sulfatide- and SQDG-mimetics as small molecular weight selectin inhibitors

Small molecular weight sulfatide analogs were synthesised and tested in cell-based selectin mediated adhesion assays. The ceramide moiety of sulfatides could be replaced by simple glycerol ethers to obtain potent mimetics. The specific activity of these i

Synthesis of Chiral Diether and Tetraether Phospholipids: Regiospecific Ring Opening of Epoxy Alcohol Intermediates Derived from Asymmetric Epoxidation

Diether and tetraether phospholipids have been synthesized using chiral epoxy alcohol starting materials (e.g. glycidol 3-nitrobenzenesulfonate esters or tert-butyldiphenylsilyl ethers).These chiral precursors provide control over the stereochemistry, sub

Inhibition of human erythrocyte membrane phosphatidylinositol 4-kinase by phospholipid analogues

Analogues of phosphatidylinositol (PtdIns, 1) have been synthesized to investigate the structural requirements for inhibition of a PtdIns 4-kinase obtained from human erythrocyte membranes. While the presence of either D-1 or D-3 stereochemistry in the inositol moiety greatly influences the degree of inhibition produced by PtdIns analogues, the stereochemistry of the glycerol moiety is of little consequence. Neither structural feature however, makes a significant contribution to binding affinity. Competitive inhibitory activity was found to be retained (or even enhanced) in substantially simpler analogues consisting of 1 or 2 hydrocarbon chains attached to a charged phosphate head group, such as in the phosphatidic acids, 24 and 26. The observation that the phosphatidylinositol 4-phosphate (PtdIns 4P) and phosphatidic acid analogues (eg, 16 or 17, and 26 respectively) inhibit PtdIns 4-kinase may suggest that such species have a regulatory role in PtdIns turnover.