Iomol Chem. 2006; four:1746754. [PubMed: 16633567] 14. Wang M, Pinnamaraju S, Ranganathan R, Hajdu J. Chem Phys Lipids. 2013; 172:785. [PubMed: 23727005] 15. (a) Chen HJ, Chen CY, Gao P, Wu Y. Tetrahedron. 2013; 69:9848851.(b) Chen CY, Han WB, Chen HJ, Wu YK, Gao P. Eur J Org Chem. 2013:4311318. 16. Ishihara K, Kurihara H, Yamamoto H. J Org Chem. 1993; 58:3791793. 17. Beneath the experimental circumstances, maintaining the temperature at 0 , and using the slow rate of addition with the catalyst, the reaction proceeded with higher regioselectivity, making 30 of the two,3-(bis)phenoxyacetyl ester as the only by-product that could effortlessly be separated by silica gel chromatography. 18. The tetrahydropyranyl compounds have been isolated as diastereomeric mixtures and they have been employed as such within the subsequent step for phosphorylation on the key hydroxyl group. 19. (a) Kim UT, Hajdu J. J Chem Soc, Chem Commun. 1993:702.(b) Marx MH, Piantadosi C, Noseda A, Daniel LW, Modest EJ. J Med Chem. 1988; 31:85863. [PubMed: 3162534] 20. The phospholipids had been obtained in higher yield, nonetheless, isolation with the products purified by silica gel chromatography frequently final results in substantial losses in recovery, because of irreversible adsorption of phospholipids around the silica gel columns, and yields of 500 are often realized; see: Blank ML, Robinson M, Snyder F.Ketoconazole Snyder F. Platelet Activating Element and Associated Lipid Mediators. Plenum PressNew York, NY1987:332. 21. Rosseto R, Hajdu J. Tetrahedron Lett. 2005; 46:2941944. 22. Ranganathan R, Tcacenco CM, Rosseto R, Hajdu J. Biophys Chem. 2006; 122:799. [PubMed: 16556477] 23. Correia-Ledo D, Arnold AA, Mauzeroll J. J Am Chem Soc. 2010; 132:151205123. [PubMed: 20932007] 24. Singh J, Ranganathan R, Hajdu J. Anal Biochem. 2010; 407:25360. [PubMed: 20727845] 25. Balet C, Clingman KA, Hajdu J. Biochem Biophys Res Commun. 1988; 150:56167. [PubMed: 3124835] 26. Dittmer JC, Lester RL. J Lipid Res. 1964; 5:12627. [PubMed: 14173318]NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptTetrahedron. Author manuscript; offered in PMC 2015 May perhaps 13.Rosseto and HajduPageNIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptFigure 1.Hydrolytic cleavage of naturally occurring phospholipids by the four phospholipases.Tetrahedron. Author manuscript; out there in PMC 2015 May possibly 13.Rosseto and HajduPageNIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptTetrahedron.Vancomycin hydrochloride Author manuscript; accessible in PMC 2015 May well 13.PMID:23715856 Figure 2.Structures of the glyceric acid precursor and also the phospholipid targets.Rosseto and HajduPageNIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptFigure three.Hydrolysis with the synthetic probes by PLA2.Tetrahedron. Author manuscript; available in PMC 2015 Could 13.Rosseto and HajduPageNIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptTetrahedron. Author manuscript; accessible in PMC 2015 Could 13.Scheme 1.Reagents and situations: (a) 1 M KOH / MeOH; (b) ROH, DCC-DMAP, CH2Cl2; (c) CH3(CH2)11NH2, DCC-DMAP, CH2Cl2, (d) HCl, aq. dioxane. (e) (C6H5)3CCl, two,four,6trimethylpyridine, CH2Cl2 (f) C6H5OCH2COCl, 2,four,6-trimethylpyridine, CHCl3; (g) (C6H5)3CCl, pyridine, CHCl3;(h) (i) 10-(7-mercapto-4-methylcoumarin)decanol, DCCDMAP, CHCl3, (ii) HCl, aq.dioxane); (i) (I) DHP-PPTS, CH2Cl2, (II) tert.-butylamine, (CHCl3-MeOH 1:1).Rosseto and HajduPageNIH-PA Author ManuscriptScheme two.Reagents and conditions: (a) (i) ethylene chlorophosphate, Et3N, benzene,.