:1). four.five.5. 2-((12-(ferrocenyl)carboxamidododecyl)oxy)-2-oxo-3-((12-((4-methyl-2oxo-2H-chromen-7-yl)thio)dodecyl)oxy)-3-oxopropyl phosphocholine (28)– Yield: 58 . IR (CHCl3): 3350, 1735 br, 1650, 1540m, 1208 cm-1; 1H NMR (CDCl3, 200 MHz) 1.24 (br s, 30H), 1.58 (m, 8H), two.37 (br s, 5H), two.94 (t, 2H, J = 7.two Hz), three.34 (br m, 10H), three.80 (m, 2H), four.05?.16 (br s, 12H), 4.28 (br s, 4H), 4.69 (br s, 2H), 5.22 (m, 1H), 6.17 (br s, 1H), 7.04?.55 (m, 3H). 13C NMR (CDCl3, 50 MHz) 15.0, 18.5, 24.7, 25.eight 26.9, 28.four, 28.6, 28.eight, 29.0, 29.4, 29.9, 32.0, 33.7, 38.4, 54.four, 59.4, 65.eight, 68.0, 69.6, 70.2, 72.0, 113.five, 116.8, 122.8, 124.five, 143.eight, 152.three, 153.8, 160.6, 168.1, 168.7, 170.0, 173.0. 31P NMR (CDCl3, 160 MHz, pyrophosphate ref. ext.): No signal was observed, a broad area around zero. Rf (CHCl3/MeOH/H2O 65:25:4) 0.57. Anal. Cald for C53H79FeN2O11PS?H2O: C, 59.21; H, 7.78; N, 2.61 Found: C, 59.28; H, 7.70; N, two.25. MS MH+ C53H79FeN2O11PSH Calcd: 1039.BODIPY-FL supplier 4569, Found: 1039.4593. []D20 -4.4?(c 0.95, CHCl3/MeOH four:1). four.six. Enzymatic hydrolysis in the phospholipids 19, 20, 26?eight four.6.1–In a standard experiment to a sample of phosphocholine (2.five mg, two.5 mol) was added to a answer of four.1 mL Tris buffer (0.05 M, pH eight.50), containing 0.1 mL Triton X-100 and 50 mM CaCl2. The mixture was vortexed, followed by incubation of your resulting dispersion at 40 for ten min.Formula of 2-Bromo-4-chloro-6-methoxypyridine within a continuous temperature water-bath. To the optically clear dispersion that resulted was added bee-venom phospholipase A2 (eight g in 45 L buffer) to initiate the reaction. The reaction mixture was kept at 40 , and formation in the products was analyzed by thin layer chromatography, (CHCl3/MeOH/H2O, 65:25:4). The compounds have been visualized by UV-absorption, fluorescence, iodine adsorption, and molybdic acid spray. TLC evaluation showed comprehensive hydrolysis for every substrate inside the series of your synthetic phospholipids.PMID:35991869 Identity with the items was confirmed with authentic samples from the lysophospholipids plus the labeled fatty acids.NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptAcknowledgmentsWe are grateful towards the National Institutes of Overall health, grant 1SC3GM09878 for monetary support.References and notes1. Bhattacharya S, Biswas J. Langmuir. 2010; 26:4642?654. [PubMed: 19842629]Tetrahedron. Author manuscript; obtainable in PMC 2015 May perhaps 13.Rosseto and HajduPage2. Skaug MJ, Longo ML, Faller R. J Phys Chem B. 2011; 115:8500?505. [PubMed: 21644587] 3. Dennis EA, Cao J, Hsu HY, Magrioti V, Kotokos G. Chem Rev. 2011; 111:6130?185. [PubMed: 21910409] four. (a) Murakami M, Taketomi Y, Sato H, Yamamoto K. J Biochem. 2011; 150:233?55. [PubMed: 21746768] (b) Murakami M, Taketomi Y, Miki Y, Sato H, Hirabayashi T, Yamamoto K. Prog Lipid Res. 2011; 50:152?92. [PubMed: 21185866] 5. Lambeau G, Gelb MH. Annu Rev Biochem. 2008; 77:495?20. [PubMed: 18405237] six. Funk CD. Science. 2001; 294:1871?875. [PubMed: 11729303] 7. Morris AJ, Smyth SS. J Lipid Res. 2013; 54:1153?157. [PubMed: 23509404] eight. Prescott SA, Zimmerman GA, Stafforini DM, McIntire TM. Annu Rev Biochem. 2000; 69:419?45. [PubMed: 10966465] 9. Murakami M, Lambeau G. Biochimie. 2013; 95:43?0. [PubMed: 23022039] 10. Schaloske RH, Dennis EA. Biochim Biophys Acta. 2006; 1761:1246?259. [PubMed: 16973413] 11. Rosseto R, Tcacenco CM, Ranganathan R, Hajdu J. Tetrahedron Lett. 2008; 49:3500?503. [PubMed: 19844592] 12. Linderoth L, Andresen TL, Jorgensen K, Madsen R, Peters GH. Biophys J. 2008; 94:14?6. [PubMed: 17827229] 13. (a) Satoh T, Hosokawa M.