22610-61-3Relevant academic research and scientific papers
Synthesis of novel nucleolipid amphiphiles
Huang, Jianguo,Ding, Daoyuan,Zhang, Zhiqiang,Shi, Bo,Liang, Yingqiu
, p. 681 - 690 (1997)
Three derivatives of uridine, thymidine and adenosine with one or two stearoyl chains, and three kinds of lipids with one or two nucleic acid bases were synthesized, which can form a stable monolayer at the air-water interface.
Development of isotope-enriched phosphatidylinositol-4- And 5-phosphate cellular mass spectrometry probes
Joffrin, Amélie M.,Saunders, Alex M.,Barneda, David,Flemington, Vikki,Thompson, Amber L.,Sanganee, Hitesh J.,Conway, Stuart J.
, p. 2549 - 2557 (2021/03/01)
Synthetic phosphatidylinositol phosphate (PtdInsPn) derivatives play a pivotal role in broadening our understanding of PtdInsPnmetabolism. However, the development of such tools is reliant on efficient enantioselective and regioselective synthetic strategies. Here we report the development of a divergent synthetic route applicable to the synthesis of deuterated PtdIns4Pand PtdIns5Pderivatives. The synthetic strategy developed involves a key enzymatic desymmetrisation step using Lipozyme TL-IM. In addition, we optimised the large-scale synthesis of deuteratedmyo-inositol, allowing for the preparation of a series of saturated and unsaturated deuterated PtdIns4Pand PtdIns5Pderivatives. Experiments in MCF7 cells demonstrated that these deuterated probes enable quantification of the corresponding endogenous phospholipids in a cellular setting. Overall, these deuterated probes will be powerful tools to help improve our understanding of the role played by PtdInsPnin physiology and disease.
Stereochemistry, lipid length and branching influences Mincle agonist activity of monoacylglycerides
Khan, Ayesha,Braganza, Chriselle D.,Kodar, Kristel,Timmer, Mattie S. M.,Stocker, Bridget L.
, p. 425 - 430 (2020/02/03)
Herein, we report on the synthesis of a series of enantiomerically pure linear, iso-branched, and α-branched monoacyl glycerides (MAGs) in 63-72% overall yield. The ability of the MAGs to signal through human macrophage inducible C-type lectin (hMincle) using NFAT-GFP reporter cells was explored, as was the ability of the compounds to activate human monocytes. From these studies, MAGs with an acyl chain length ≥C22 were required for Mincle activation and the production of interleukin-8 (IL-8) by human monocytes. Moreover, the iso-branched MAGs led to a more pronounced immune response compared to linear MAGs, while an α-branched MAG containing a C-32 acyl chain activated cells to a higher degree than trehalose dibehenate (TDB), the prototypical Mincle agonist. Across the compound classes, the activity of the sn-1 substituted isomers was greater than the sn-3 counterparts. None of the representative compounds were cytotoxic, thus mitigating cytotoxicity as a potential mediator of cellular activity. Taken together, 6h (sn-1, iC26+1), 8a (sn-1, C32) and 8b (sn-3, C32) exhibited the best immunostimulatory properties and thus, have potential as vaccine adjuvants.
Optically active monoacylglycerols: Synthesis and assessment of purity
Chen, Chao-Yuan,Han, Wei-Bo,Chen, Hui-Jun,Wu, Yikang,Gao, Po
, p. 4311 - 4318 (2013/07/26)
Despite their simple structures, synthesis of 1(or 3)-acyl-sn-glycerols remains a challenge that cannot be ignored because of facile acyl migrations, which not only complicate the synthesis but also make direct GC or HPLC analysis unfeasible. Assessment of the optical purity of monoacylglycerols has, to date, relied almost exclusively on specific rotation data, which are small in value and thus insensitive to impurities. Now, a simple means to "magnify" the small specific rotations has been found, along with practical methods for the measurement of both 1,2-and 1,3-acyl migrations, which offer a convenient and straightforward alternative to Mori's NMR analysis of Mosher esters. With the aid of these methods, a range of conditions for deacetonide removal were examined en route to the synthesis of two natural monoacylglycerols. Refined hydrolysis conditions, along with useful knowledge about the solubility and reactivity of substrates with an ultra long alkyl chain are also presented. Copyright
Pheromone synthesis. Part 253: Synthesis of the racemates and enantiomers of triglycerides of male Drosophila fruit flies with special emphasis on the preparation of enantiomerically pure 1-monoglycerides
Mori, Kenji
, p. 8441 - 8449 (2012/10/07)
The racemates and enantiomers of triglycerides 1aee (2,3-ditigloyloxypropyl esters of palmitic, palmitoleic, stearic, oleic, and linoleic acids) of male Drosophila fruit flies were synthesized in three steps from the racemate and enantiomers of 2,3-acetoneglycerol (2) via 1-monoglycerides 4aee derived from the above fatty acids. Appropriate conditions were established for the preparation of enantiomerically pure 1-monoglycerides 4aee, and their enantiomeric purities were determined by NMR analysis of the corresponding bis-(R)-MTPA esters.
Chemoenzymatic synthesis of enantiopure structured triacylglycerols
Kristinsson, Bj?rn,Haraldsson, Gudmundur G.
experimental part, p. 2178 - 2182 (2009/06/18)
A highly efficient chemoenzymatic method for the synthesis of enantiopure ABC-type asymmetrically structured triacylglycerols has been developed starting from enantiopure (S)-solketal and involving two lipase steps. Georg Thieme Verlag Stuttgart.
Lp-PLA2 inhibitory activities of fatty acid glycerols isolated from Saururus chinensis roots
Woo, Song Lee,Mi, Jeong Kim,Beck, Young-Il,Park, Yong-Dae,Jeong, Tae-Sook
, p. 3573 - 3575 (2007/10/03)
(R)-Glycerol-monolinoleate 4 and (R)-glycerol-monostearate 5 were isolated from the ethyl acetate extracts of Saururus chinensis roots and (R)- or (S)-fatty acid glycerols 4 and 5 were synthesized for confirming their structures and evaluating their inhibitory activities against Lp-PLA 2. The (R)-4 and (S)-4 exhibited Lp-PLA2 inhibitory activities with IC50 values of 45.0 and 52.0 μM, respectively.
Comprehensive and uniform synthesis of all naturally occurring phosphorylated phosphatidylinositols
Kubiak, Robert J.,Bruzik, Karol S.
, p. 960 - 968 (2007/10/03)
Studies of cellular signal transduction mechanisms involving receptor-mediated generation of inositol phosphates and phosphorylated phosphatidylinositols require easy access to these naturally occurring products. Although numerous synthetic methods have been developed during the past decade, most of these methods suffer from excessive length and lack of generality. In this work we describe the comprehensive and uniform synthesis of all naturally occurring phosphatidylinositols such as phosphatidylinositol, phosphatidylinositol 3-phosphate, 4-phosphate, 5-phosphate, 3,4-bisphosphate, 3,5-bisphosphate, 4,5-bisphosphate, and 3,4,5-trisphosphate, featuring both saturated and unsaturated fatty acid chains.
Xanthen-9-ylidene protecting groups in glycerol chemistry
Reese, Colin B.,Yan, Hongbin
, p. 1807 - 1815 (2007/10/03)
The preparation of racemic, (S)- and (R)-1,2-O-(xanthen-9-ylidene)glycerol 17a, 20a and 23a and racemic, (S)and (R)-1,2-O-(2,7-dimethylxanthen-9-ylidene)glycerol 17b, 20b and 23b is reported. The racemic derivatives 17a and 17b are converted into their st
Synthesis of naturally occurring phosphatidylinositol 3,4,5-trisphosphate [PtdIns(3,4,5)P3] and its diastereoisomers
Gaffney, Piers R.J.,Reese, Colin B.
, p. 192 - 205 (2007/10/03)
The chemical synthesis of naturally occurring phosphatidylinositol 3,4,5-triphosphate [PtdIns(3,4,5)P3] and its diastereoisomers was discussed. In the first stage, the preparation of the required enantiomeric 1,2-di-O-acylglycerol derivatives was done. The second stage involved the preparation of suitably protected enantiomeric myo-inositol 1-phosphates. The glycerol and inositol building blocks were coupled together and the 3-, 4- and 5-hydroxy functions of the inositol residues in the coupled products were phosphorylated. Finally, the protecting groups were removed to give PtdIns(3,4,5)P3 and its diastereoisomers.
