Discrimination between the regioisomeric 1,2- and 1,3- diacylglycerophosphocholines by phospholipases

Chemistry and Physics of Lipids

Volumn 164, Issue 3, 2011, Pages 196-204

  Mansfeld, Johanna ^a   Brandt, Wolfgang ^b   Haftendorn, Regine ^a,c   Schöps, Regina ^a   Ulbrich Hofmann, Renate ^a  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

^b LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

^c Genzyme GmbH   (Germany)

Author keywords

1,3 Diacylglycero 2 phosphocholines; Phospholipase C; Phospholipase D; Secretory phospholipases A2

Indexed keywords

1,2 DIACYLGLYCEROPHOSPHOCHOLINE; 1,3 DIACYLGLYCERO 2 PHOSPHOCHOLINE; DEOXYCHOLATE SODIUM; PHOSPHATIDYLCHOLINE; PHOSPHOLIPASE A2; PHOSPHOLIPASE C; PHOSPHOLIPASE D; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CATALYSIS; CONTROLLED STUDY; CRYSTAL STRUCTURE; ENZYME CONFORMATION; ENZYME KINETICS; ENZYME STRUCTURE; ENZYME SUBSTRATE; HYDROLYSIS; ISOMER; PRIORITY JOURNAL;

ANIMALS; ARABIDOPSIS; BACILLUS CEREUS; BEE VENOMS; BEES; BINDING SITES; COBRA; COBRA VENOMS; PANCREAS; PHOSPHATIDYLCHOLINES; PHOSPHOLIPASES A2; STEREOISOMERISM; SUBSTRATE SPECIFICITY; SWINE; TYPE C PHOSPHOLIPASES;

APOIDEA; ARABIDOPSIS THALIANA; BACILLUS CEREUS; BRASSICA OLERACEA VAR. CAPITATA; STREPTOMYCES; SUS;

EID: 79952699565     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2010.12.009     Document Type: Article

References (53)

1. Berg, O.G., Jain, M.K., 2002. In: Burgoyne, R.D., Morgan, A. (Eds.), Interfacial Enzyme Kinetics. John Wiley, Chichester, UK, 301 pp.
2. 2-paradigm for interfacial binding. Biochemistry 43, 7999-8013.
3. 2. Biochemistry 48, 3209-3218.
4. Berman, H.M., Westbrook, J., Feng, Z., Gilliland, G., Bhat, T.N., Weissig, H., Shindyalov, I.N., Bourne, P.E., 2000. The Protein Data Bank. Nucleic Acids Res. 28, 235-242. (Pubitemid 30047768)
5. 2 structure/function, mechanism, and signaling. J. Lipid Res. 50 (Suppl.), S237-242.
6. Clark, M., 2005. Generalized fragment-substructure based property prediction method. J. Chem. Inf. Model. 45, 30-38.
7. de Haas, G.H., van Deenen, L.L., 1964. The site of action of phospholipase A on β-lecithins. Biochim. Biophys. Acta 84, 469-471.
8. de Haas, G.H., van Deenen, L.L., 1965. Structural identification of isomeric lysolecithins. Biochim. Biophys. Acta 106, 315-325.
9. Dippe, M., Ulbrich-Hofmann, R., 2009. Substrate specificity in phospholipid transformations by plant phospholipase D isoenzymes. Phytochemistry 70, 361-365.
10. Dittrich, N., Haftendorn, R., Ulbrich-Hofmann, R., 1998. Hexadecylphosphocholine and 2-modified 1,3-diacylglycerols as effectors of phospholipase D. Biochim. Biophys. Acta 1391, 265-272.
11. Dluhy, R.A., Chowdhry, B.Z., Cameron, D.G., 1985. Infrared characterization of conformational differences in the lamellar phases of 1,3-dipalmitoyl-sn-glycero-2-phosphocholine. Biochim. Biophys. Acta 821, 437-444.
12. El-Sayed, M.Y., DeBose, C.D., Coury, L.A., Roberts, M.F., 1985. Sensitivity of phospholipase C (Bacillus cereus) activity to phosphatidylcholine structural modifications. Biochim. Biophys. Acta 837, 325-335.
13. Frense, D., Haftendorn, R., Ulbrich-Hofmann, R., 1995. 2-modified 1,3-diacylglycerols as new surfactants for the formation of reverse micelles. Chem. Phys. Lipids 78, 81-87.
14. Gasteiger, J., Marsili, M., 1978. New model for calculating atomic charges in molecules. Tetrahedron Lett., 3181-3184.
15. Gasteiger, J., Marsili, M., 1980. Iterative partial equalization of orbital electronegativity - a rapid access to atomic charges. Tetrahedron 36, 3219-3228.
16. 2 and an octanoate complex. J. Biol. Chem. 284, 19371-19379.
17. Haftendorn, R., Schwarze, G., Ulbrich-Hofmann, R., 2000. 1,3-Diacylglycero-2-phosphocholines - synthesis, aggregation behaviour and properties as inhibitors of phospholipase D. Chem. Phys. Lipids 104, 57-66.
18. Haftendorn, R., Ulbrich-Hofmann, R., 1995. Synthesis of 2-modified 1,3-diacylglycerols. Tetrahedron 51, 1177-1186.
19. Haftendorn, R., Ulbrich-Hofmann, R., 2002. Activity of phospholipase C in two-phase systems. Anal. Biochem. 306, 144-147.
20. Hatanaka, T., Negishi, T., Kubota-Akizawa, M., Hagishita, T., 2002. Purification, characterization, cloning and sequencing of phospholipase D from Streptomyces septatus TH-2. Enzyme Microb. Technol. 31, 233-241.
21. 2 action. J. Biol. Chem. 259, 5734-5739.
22. Hirche, F., Koch, M.H.H., König, S., Wadewitz, T., Ulbrich-Hofmann, R., 1997. The influence of organic solvents on phospholipid transformations by phospholipase D in emulsion systems. Enzyme Microb. Technol. 20, 453-461.
23. Hoffmann, G.E., Schmidt, D., Bastian, B., Guder, W.G., 1986. Photometric determination of phospholipase A. J. Clin. Chem. Clin. Biochem. 24, 871-875.
24. Hough, E., Hansen, L.K., Birknes, B., Jynge, K., Hansen, S., Hordvik, A., Little, C., Dodson, E., Derewenda, Z., 1989. High-resolution (1.5 Å) crystal structure of phospholipase C from Bacillus cereus. Nature 338, 357-360.
25. Hough, E., Hansen, S., 1994. Structural aspects of phospholipase C from Bacillus cereus and its reaction mechanism. In: Woolley, P., Petersen, S.B. (Eds.), Lipases. Cambridge University Press, Cambridge, pp. 95-118.
26. 2 from Naja naja sagittifera with a strong anticoagulant activity. Toxicon 46, 865-875.
27. Jones, G., Willett, P., Glen, R.C., Leach, A.R., Taylor, R., 1997. Development and validation of a genetic algorithm for flexible docking. J. Mol. Biol. 267, 727-748.
28. Kunitake, T., Okahata, Y., Tawaki, S.I., 1984. Bilayer characteristics of 1,3-dialkyl- and 1,3-diacyl-rac-glycero-2-phosphocholines. J. Colloid Interface Sci. 103, 190-201.
29. Kuppe, K., Kerth, A., Blume, A., Ulbrich-Hofmann, R., 2008. Calcium-induced membrane microdomains trigger plant phospholipase D activity. ChemBiochem 9, 2853-2859.
30. Laskowski, R.A., MacArthur, M.W., Moss, D.S., Thornton, J.M., 1993. PROCHECK: a program to check the stereochemical quality of protein structures. J. Appl. Crystallogr. 26, 283-291.
31. Leiros, I., McSweeney, S., Hough, E., 2004. The reaction mechanism of phospholipase Dfrom Streptomyces sp. strain PMF. Snapshots along the reaction pathway reveal a pentacoordinate reaction intermediate and an unexpected final product. J. Mol. Biol. 339, 805-820.
32. Lewis, K.A., Bian, J.R., Sweeney, A., Roberts, M.F., 1990. Asymmetric short-chain phosphatidylcholines: defining chain binding constraints in phospholipases. Biochemistry 29, 9962-9970. (Pubitemid 20348533)
33. 2 activity toward phospholipids with sn-1 substitutions. Biophys. J. 94, 14-26.
34. MacKerell Jr., A.D., Bashford, D., Bellott, M., Dunbrack Jr., R.L., Evanseck, J., Field, M.J., Fischer, S., Gao, J., Guo, H., Ha, S., Joseph, D., Kuchnir, L., Kuczera, K., Lau, F.T.K., Mattos, C., Michnick, S., Ngo, T., Nguyen, D.T., Prodhom, B., Reiher, W.E., Roux, B., Schlenkrich, M., Smith, J., Stote, R., Straub, J., Watanabe, M., Wiorkiewicz-Kuczera, J., Yin, D., Karplus, M., 1998. All-atom empirical potential for molecular modeling and dynamics studies of protein. J. Phys. Chem. B 102, 3586-3616.
35. 2: perspectives on biotechnological applications. Biotechnol. Lett. 31, 1373-1380.
36. 2 from Arabidopsis thaliana: insights into the three-dimensional structure and the amino acids involved in catalysis. Biochemistry 45, 5687-5694.
37. Mansfeld, J., Ulbrich-Hofmann, R., 2009. The modulation of phospholipase D activity in vitro. Biochim. Biophys. Acta 1791, 913-926.
38. 2-α from Arabidopsis thaliana: functional parameters and substrate preference. Chem. Phys. Lipids 150, 156-166.
39. Nissink, J.W., Murray, C., Hartshorn, M., Verdonk, M.L., Cole, J.C., Taylor, R., 2002. A new test set for validating predictions of protein-ligand interaction. Proteins 49, 457-471. (Pubitemid 35388132)
40. Pellegrini, E., Field, M.J., 2002. A generalized-born solvation model for macromolecular hybrid-potential calculations. J. Phys. Chem. A 106, 1316-1326.
41. 2 hydrolysis of phospholipid analogues is dependent on water accessibility to the active site. J. Am. Chem. Soc. 129, 5451-5461.
42. Ponting, C.P., Kerr, I.D., 1996. A novel family of phospholipase D homologues that includes phospholipid synthases and putative endonucleases: identification of duplicated repeats and potential active site residues. Protein Sci. 5, 914-922. (Pubitemid 26139179)
43. 2 and phospholipase C in a mixed micellar system. J. Biol. Chem. 253, 1252-1257.
44. Schäffner, I., Rücknagel, K.-P., Mansfeld, J., Ulbrich-Hofmann, R., 2002. Genomic structure, cloning and expression of two phospholipase D isoenzymes from white cabbage. Eur. J. Lipid Sci. Technol. 104, 79-87.
45. Seelig, J., Dijkman, R., de Haas, G.H., 1980. Thermodynamic and conformational studies on sn-2-phosphatidylcholines in monolayers and bilayers. Biochemistry 19, 2215-2219.
46. Sippl, M.J., 1993. Recognition of errors in three-dimensional structures of proteins. Proteins 17, 355-362. (Pubitemid 23358545)
47. Slotboom, A.J., Verger, R., Verheij, H.M., Baartmans, P.H., Deenen, L.L., Haas, G.H., 1976. Application of enantiomeric 2-sn-phosphatidylcholines in interfacial enzyme kinetics of lipolysis. Chem. Phys. Lipids 17, 128-147.
48. Sung, T.C., Roper, R.L., Zhang, Y., Rudge, S.A., Temel, R., Hammond, S.M., Morris, A.J., Moss, B., Engebrecht, J., Frohman, M.A., 1997. Mutagenesis of phospholipase D defines a superfamily including a trans-Golgi viral protein required for poxvirus pathogenicity. EMBO J. 16, 4519-4530. (Pubitemid 27326589)
49. Tripos Inc., S.H.R.S.L., MO, USA, 2007. SYBYL Computer Program. Version 7.0.
50. Ulbrich-Hofmann, R., 2000. Phospholipases used in lipid transformations. In: Bornscheuer, U.T. (Ed.), Enzymes in Lipid Modification. Wiley-VCH, Weinheim, pp. 219-262.
51. Ulbrich-Hofmann, R., 2003. Enzyme-catalysed transphosphatidylation. Eur. J. Lipid Sci. Technol. 105, 305-307.
52. Verdonk, M.L., Cole, J.C., Hartshorn, M.J., Murray, C.W., Taylor, R.D., 2003. Improved protein-ligand docking using GOLD. Proteins 52, 609-623. (Pubitemid 37034158)
53. Wieder, T., Reutter, W., Orfanos, C.E., Geilen, C.C., 1999. Mechanisms of action of phospholipid analogs as anticancer compounds. Prog. Lipid Res. 38, 249-259.