65914-84-3Relevant academic research and scientific papers
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.
The fatty acid composition of diacylglycerols determines local signaling patterns
Nadler, Andre,Reither, Gregor,Feng, Suihan,Stein, Frank,Reither, Sabine,Mueller, Rainer,Schultz, Carsten
supporting information, p. 6330 - 6334 (2013/07/05)
Caged compounds are designed to release biologically active signaling molecules with temporal, spatial, and even subcellular resolution. But how localized does the signal stay? Using the example of diacylglycerol, some signal responses (PKC) are shown to
Regioselective approach to phosphatidylinositol 3,5-bisphosphates: Syntheses of the native phospholipid and biotinylated short-chain derivative
Anderson, Regan J.,Osborne, Shona L.,Meunier, Frederic A.,Painter, Gavin F.
supporting information; experimental part, p. 3541 - 3551 (2010/09/03)
Figure presented A selective bis-silylation of 1D-O-TBDPS-myo-inositol leads to a 1,3,5-trisubstituted inositol, which can be advanced to the headgroup of phosphatidylinositol-3,5-bisphosphate [PI(3,5)P2]. A mild, regioselective method for construction of the diacylglycerol moiety containing differing fatty acid chains, including the naturally occurring lipids, was developed. Their union in the synthesis of the cell-signaling molecule PI(3,5)P2 containing the sn-1-stearoyl and sn-2-arachidonoyl groups is described. The methodology was also used to generate dioctanoyl-PI(3,5)P 2 and a previously unreported biotin-PI(3,5)P2 conjugate, which was coupled to neutravidin beads and used to pull down PI(3,5)P 2-binding proteins from the cytosolic extract of adrenal neurosecretory cells. We report the specific pull-down of the PI(3,5)P 2-binding protein svp1p, a known PI(3,5)P2 effector involved in membrane trafficking.
The total synthesis of 2-O-arachidonoyl-1-O-stearoyl-sn-glycero-3-phosphocholine-1,3,1′-13C3 and -2,1′-13C2 by a novel chemoenzymatic method
Duclos Jr., Richard I.
experimental part, p. 102 - 109 (2010/06/19)
2-O-Arachidonoyl-1-O-stearoyl-sn-glycero-3-phosphocholine was synthesized with carbon-13 enrichment of the three glycerol carbons and the carbonyl of the stearoyl group. Phospholipase A2 was utilized to give optically pure lyso-PC, and only 3% acyl migration occurred during reacylation with arachidonic acid anhydride. This phospholipid is an important biosynthetic precursor of arachidonic acid metabolites as well as the endocannabinoid 2-arachidonoylglycerol (2-AG), and is now available for NMR studies.
First synthesis of natural phosphatidyl-β-d-glucoside
Greimel, Peter,Ito, Yukishige
, p. 3562 - 3566 (2008/09/19)
Herein, we report the chemical synthesis of naturally occurring mammalian phosphatidyl-β-d-glucoside (PtdGlc), in order to confirm the proposed structure and to clarify its stereochemistry. We designed a convergent synthetic strategy, suitable to prepare
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.
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.
Preparation of 2-O-arachidonoyl-1-O-stearoyl-sn-glycerol and other di-O-acyl glycerol derivatives
Gaffney, Piers R.J.,Reese, Colin B.
, p. 2539 - 2542 (2007/10/03)
R(-)-2,3- and S(+)-1,2-O-Isopropylidene-sn-glycerols (4 and 9) are converted into 2-O-arachidonoyl-1-O-stearoyl and 2-O-arachidonoyl-3-O-stearoyl-sn-glycerols (2 and 3, respectively); glycerol is also converted into its racemic 1,2- and its symmetrical 13-di-O-linoleoyl derivatives (14 and 17, respectively).
Cosmetic composition
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, (2008/06/13)
A composition suitable for topical application to mammalian skin and hair for inducing, maintaining or increasing hair growth comprises a hair growth promoter chosen from glutamine derivatives and salts thereof. The composition preferably also comprises an activity enhancer which may be chosen from hair growth stimulants, penetration enhancers and cationic polymers.
