Enzyme-assisted total synthesis of the optical antipodes D-myo-inositol 3,4,5-trisphosphate and D-myo-inositol 1,5,6-trisphosphate: Aspects of their structure-activity relationship to biologically active inositol phosphates

Journal of Medicinal Chemistry

Volumn 42, Issue 7, 1999, Pages 1262-1273

  Adelt, Stephan ^a   Plettenburg, Oliver ^a   Stricker, Rolf ^b   Reiser, Georg ^b   Altenbach, Hans Josef ^a   Vogel, Günter ^a  

^a UNIVERSITY OF WUPPERTAL   (Germany)

^b OTTO VON GUERICKE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING PROTEIN; CYCLOHEXENE DERIVATIVE; ENZYME; INOSITOL; INOSITOL TRISPHOSPHATE; MYO INOSITOL 1,5,6 TRIPHOSPHATE; MYO INOSITOL 3,4,5 TRIPHOSPHATE; PHOSPHATASE; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; DICTYOSTELIUM DISCOIDEUM; ENANTIOMER; ENZYME ACTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR RECOGNITION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ACTIVITY RELATION; SWINE; SYNTHESIS; X RAY;

ACID ANHYDRIDE HYDROLASES; ANIMALS; CEREBELLUM; DICTYOSTELIUM; GUINEA PIGS; INOSITOL PHOSPHATES; RECEPTORS, CYTOPLASMIC AND NUCLEAR; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0033535534     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm981113k     Document Type: Article

References (62)

1. Berridge, M. J. Inositol trisphosphate and calcium signaling. Nature (London) 1993, 361, 315-325.
2. Downes, C. P.; Macphee, C. H. myo-Inositol metabolites as cellular signals. Eur. J. Biochem. 1990, 193, 1-18.
3. Woodcock, E. A. Inositol phosphates and inositol phospholipids: how big is the iceberg? Mol. Cell. Endocrinol. 1997, 127, 1-10.
4. Fukuda, M.; Mikoshiba, K. The function of inositol high polyphosphate binding proteins. BioEssays 1997, 19, 593-603.
5. Takeuchi, H.; Kanematsu, T.; Misumi, Y.; Sakane, F.; Konishi, H.; Kikkawa, U.; Watanabe, Y.; Katan, M.; Hirata, M. Distinct specificity in the binding of inositol phosphates by pleckstrin homology domains of pleckstrin, RAC-protein kinase, diacylglycerol kinase and a new 130 kDa protein. Biochim. Biophys. Acta 1997, 1359, 275-285.
6. Frech, M.; Andjelkovic, M.; Ingley, E.; Reddy, K K.; Falck, J. R.; Hemmings, B. A. High Affinity Binding of Inositol Phosphates and Phosphoinositides to the Pleckstrin Homology Domain of RAC/Protein Kinase B and Their Influence on Kinase Activity. J. Biol. Chem. 1997, 272, 8474-8481.
7. Ferguson, K. M.; Lemmon, M. A.; Schlessinger, J.; Sigler, P. B. Structure of the High Affinity Complex of Inositol Trisphosphate with a Phospholipase C Pleckstrin Homology Domain. Cell 1995, 83, 1037-1046.
8. Hirata, M.; Kanematsu, T.; Takeuchi, H.; Yagisawa, H. Pleckstrin Homology Domain as an Inositol Compound Binding Module. Jpn. J. Pharmacol. 1998, 76, 255-263.
9. Touhara, K.; Inglese, J.; Pitcher, J. A.; Shaw, G.; Lefkowitz, R. J. Binding of G Protein βγ-Subunits to Pleckstrin Homology Domains. J. Biol. Chem. 1994, 269, 10217-10220.
10. Yao, L.; Suzuki, H.; Ozawa, K.; Deng, J.; Lehel, C.; Fukamachi, H.; Anderson, W. B.; Kawakami, Y.; Kawakami, T. Interactions between Protein Kinase C and Pleckstrin Homology Domains. J. Biol. Chem. 1997, 272, 13033-13039.
11. Van Haastert, P. J. M.; Van Dijken, P. Biochemistry and genetics of inositol phosphate metabolism in Dictyostelium. FEBS Lett. 1997, 410, 39-43.
12. 1 receptor stimulation in DDT1 MF-2 cells. Eur. J. Pharmacol. (Mol. Pharmacol. Sect.) 1995, 289, 463-469.
13. 4, Nature (London) 1994, 371, 711-714.
14. Eckmann, L.; Rudolf, M. T.; Ptasznik, A.; Schultz, C.; Jiang, T.; Wolfson, N.; Tsien, R.; Fierer, J.; Shears, St. B.; Kagnoff, M. F.; Traynor-Kaplan, A. E. D-myo-Inositol 1,4,5,6-tetrakisphosphate produced in human intestinal epithelial cells in response to Salmonella invasion inhibits phosphoinositide 3-kinase signaling pathways. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 14456-14460.
15. Takeuchi, H.; Kanematsu, T.; Misumi, Y.; Yaakob, H. B.; Yagisawa, H.; Ikehara, Y.; Watanabe, Y.; Tan, Z.; Shears, St. B.; Hirata, M. Localization of a high-affinity inositol 1,4,5-trisphosphate/inositol 1,4,5,6-tetrakisphosphate binding domain to the pleckstrin homology module of a new 130 kDa protein: characterization of the determinants of a structural specificity. Biochem. J. 1996, 318, 561-568.
16. Ismailov, I. I.; Fuller, C. M.; Berdiev, B. K.; Shlyonsky, V. G.; Benos, D. J.; Barrett, K. E. A biologic function for an "orphan" messenger: D-myo-Inositol 3,4,5,6-tetrakisphosphate selectively blocks epithelial calcium-activated chloride channels. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 10505-10509.
17. 3. FEBS Lett. 1997, 405, 229-236.
18. 4 receptor. Biochem. J. 1995, 305, 139-143.
19. Hammonds-Odie, L. P.; Jackson, T. R.; Profit, A. A.; Blader, I. J.; Turck, C. W.; Prestwich, G. D.; Theibert, A. B. Identification and Cloning of Centaurin-α - A novel Phosphatidylinositol 3,4,5-trisphosphate-binding Protein from Rat Brain. J. Biol. Chem. 1996, 271, 18859-18868.
20. Potter, B. V. L.; Lampe, D. Die Chemie der Inositlipid-vermittelten zellulären Signalübertragung. Angew. Chem. 1995, 107, 2085-2125.
21. Majerus, Ph. W. Inositol Phosphate Biochemistry. Annu. Rev. Biochem. 1992, 61, 225-250.
22. IP4, a high-affinity inositol(1,3,4,5)tetrakisphosphate/ phosphatidylinositol(3,4,5)trisphosphate binding protein. Biochim. Biophys. Acta 1998, 1387, 117-128.
23. Pietrusiewicz, K. M.; Salamonczyk, G. M.; Bruzik, K. S. The Synthesis of homochiral Inositol Phosphates from myo-Inositol. Tetrahedron 1992, 48, 5523-5542. Corrigendum: Pietrusiewicz, K. M.; Salamonczyk, G. M.; Bruzik, K. S. Tetrahedron 1994, 50, 573-574.
24. Pietrusiewicz, K. M.; Salamonczyk, G. M.; Bruzik, K. S. The Synthesis of homochiral Inositol Phosphates from myo-Inositol. Tetrahedron 1992, 48, 5523-5542. Corrigendum: Pietrusiewicz, K. M.; Salamonczyk, G. M.; Bruzik, K. S. Tetrahedron 1994, 50, 573-574.
25. Ozaki, S.; Ling, L.; Ogasawara, T.; Watanabe, Y.; Masato, H. A convenient chemoenzymatic synthesis of D-and L-myo-Inositol 1,4,5,6-tetrakisphosphate. Carbohydr. Res. 1994, 259, 307-310.
26. Römer, S.; Stadler, C.; Rudolf, M. T.; Schultz, C. Synthesis of D-myo-Inositol 3,4,5,6-and 1,4,5,6-Tetrakisphosphates Analogues and their Membrane-permeant Derivatives. J. Chem. Soc., Chem. Commun. 1995, 411-412. Römer, S.; Stadler, C.; Rudolf, M. T.; Jasdorf, B.; Schultz, C. Membrane-permeant analogues of the putative second-messenger myo-inositol 3,4,5,6-tetrakisphosphate. J. Chem. Soc. Perkin Trans. 1 1996, 1683-1694.
27. Römer, S.; Stadler, C.; Rudolf, M. T.; Schultz, C. Synthesis of D-myo-Inositol 3,4,5,6-and 1,4,5,6-Tetrakisphosphates Analogues and their Membrane-permeant Derivatives. J. Chem. Soc., Chem. Commun. 1995, 411-412. Römer, S.; Stadler, C.; Rudolf, M. T.; Jasdorf, B.; Schultz, C. Membrane-permeant analogues of the putative second-messenger myo-inositol 3,4,5,6-tetrakisphosphate. J. Chem. Soc. Perkin Trans. 1 1996, 1683-1694.
28. Shears, S. B. Inositol Pentakis-and Hexakisphosphate Metabolism Adds Versatility to the Action of Inositol Polyphosphates. Novel Effects on Ion Channels and Protein Traffic. In Subcellular Biochemistry, Volume 26: myo Inositol Phosphates, Phosphoinositides, and Signal Transduction; Biwas, B. B., Biwas, S., Eds.; Plenum Press: New York, 1996; pp 187-225.
29. Altenbach, H. J.; Stegelmeier, H.; Vogel, E. Einfache Stereospezifische Synthesen von anti-Benzoldioxid und anti-Benzoltrioxid. Tetrahedron Lett. 1978, 31, 3333-3334.
30. a) Altenbach, H.-J. Flexible, Stereocontrolled Routes to Sugar Mimics via Convenient Intermediates. In Antibiotics and Antiviral Compounds; Krohn, K., Kirst, H., Maas, H., Eds.; VCH: Weinheim, 1993; pp 359-372.
31. 2 Symmetric Diol Derived from p-Benzoquinone Synthesis of (+)-and (-)-Bromoxone. J. Org. Chem. 1995, 60, 6674-6675.
32. Esser, T.; Farkas, F.; Mangholz, S.; Séquin, U. Concerning the Reaction of anti-Benzene Dioxide with Various Nucleophiles. Tetrahedron 1994, 50, 3709-3720; see also ref 27.
33. Shing, T. K. M.; Tai, V. W.-F.; Tam, E. K. W.; Chung, I. H. F.; Jiang, Q. Ruthenium-Catalyzed cis-Dihydroxylation of Alkenes: Scope and Limitation. Chem. Eur. J. 1996, 2, 50-57.
34. Baldauf, S. L.; Doolittle, W. F. Origin and evolution of the slime molds (Mycetozoa). Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 12007-12012.
35. Watts, D. J.; Ashworth, J. M. Growth of Myxamoebae of the Cellular Slime Mould Dictyostelium discoideum in Axenic Culture. Biochem. J. 1970, 119, 171-174.
36. Klein, G.; Cotter, D. A.; Martin, J.-B.; Satre, M. Vanadate, an inhibitor of growth, development and endocytosis in Dictyostelium discoideum amoebae. J. Cell Sci. 1989, 94, 127-134.
37. Das, O. P.; Henderson, E. J. A novel technique for gentle lysis of eucaryotic cells isolation of plasma membranes from Dictyostelium discoideum. Biochim. Biophys. Acta 1983, 736, 45-56.
38. Dimond, R. L.; Burns, R. A.; Jordan, K. B. Secretion of Lysosomal Enzymes in the Cellular Slime Mold, Dictyostelium Discoideum. J. Biol. Chem. 1981, 256, 6565-6572.
39. Van Lookeren Campagne, M. M.; Erneux, C.; Van Eijk, R.; Van Haastert, P. J. M. Two dephosphorylation pathways of inositol 1,4,5-trisphosphate in homogenates of the cellular slime mould Dictyostelium discoideum. Biochem. J. 1988, 254, 343-350.
40. Hayakawa, T.; Suzuki, K.; Miura, H.; Ohno, T.; Igaue, I. Myoinositol Polyphosphate Intermediates in the Dephosphorylation of Phytic Acid by Acid Phosphatase with Phytase Activity from Rice Bran. Agric. Biol. Chem. 1990, 54, 279-286.
41. Lanzetta, P. A.; Alvarez, L. J.; Reinach, P. S.; Candia, O. A. An Improved Assay for Nanomole Amounts of Inorganic Phosphate. Anal. Biochem. 1979, 100, 95-97.
42. Mayr, G. W. Mass Determination of Inositol Phosphates by High-Performance Liquid Chromatography with Postcolumn Complexometry (Metal-Dye Detection). In Methods in Inositide Research; Irvine, R. F., Ed.; Raven Press: New York, 1990; pp 83-108.
43. Van Dijken, P.; Lammers, A. A.; Van Haastert, P. J. M. In Dictyostelium discoideum inositol 1,3,4,5-tetrakisphosphate is dephosphorylated by a 3-phosphatase and a 1-phosphatase. Biochem. J. 1995, 308, 127-130.
44. Nogimori, K.; Hughes, Ph. J.; Glennon, M. C.; Hodgson, M. E.; Putney, J. W., Jr.; Shears, St. B. Purification of an Inositol (1,3,4,5)-Tetrakisphosphate 3-Phosphatase Acitivity from Rat Liver and the Evaluation of its Substrate Specificity. J. Biol. Chem. 1991, 266, 16499-16506.
45. Guse, A. H.; Emmrich, F. T-cell Receptor-mediated Metabolism of Inositol Polyphosphates in Jurkat T-lymphocytes. J. Biol. Chem. 1991, 266, 24498-24502.
46. Rudolf, M. T.; Kaiser, Th.; Guse, A. H.; Mayr, G. W.; Schultz, C. Synthesis and Metabolism of the myo-Inositol Pentakisphosphates. Liebigs Ann. / Recueil 1997, 1861-1869.
47. Salamonczyk, G. M.; Pietrusiewicz, K. M. Synthesis of Enantiomerically Pure D-myo-Inositol 1,5,6-Trisphosphate. Tetrahedron Lett. 1994, 35, 4233-4234.
48. Falck, J. R.; Abdali, A. Total Synthesis of D-myo-Inositol 3,4,5-Trisphosphate and 1,3,4,5-Tetrakisphosphate. Bioorg. Med. Chem. Lett. 1993, 3, 717-720.
49. Freund, W.-D.; Mayr, G. W.; Tietz, C.; Schultz, J. E. Metabolism of inositol phosphates in the protozoan Paramecium - Characterization of a novel inositol-hexakisphosphate-dephosphorylating enzyme. Eur. J. Biochem. 1992, 207, 359-367.
50. Phillippy, B. Q.; Graf, E. Antioxidant functions of Inositol 1,2,3-Trisphosphate and Inositol 1,2,3,6-Tetrakisphosphate. Free Radical Biol. Med. 1997, 22, 939-946.
51. Shamsuddin, A. M. Inositol Phosphates have novel Anticancer Function. J. Nutr. 1995, 125, 725S-732S.
52. Hawkins, Ph. T.; Poyner, D. R.; Jackson, T. R.; Letcher, A. J.; Lander, D. A.; Irvine, R. F. Inhibition of iron-catalysed hydroxyl radical formation by inositol polyphosphates: a possible physiological function for myo-inositol hexakisphosphate, Biochem. J. 1993, 294, 929-934.
53. IP4: Comparison of Affinities of All Inositoltris-, -Tetrakis-, and -Pentakisphosphate Regioisomers. Biochem. Biophys. Res. Commun. 1996, 228, 596-604.
54. 2+ mobilization. Biochem. J. 1993, 294, 191-194.
55. Rebecchi, M. J.; Scarlata, S. Pleckstrin Homology Domains: A Common Fold with Diverse Functions. Annu. Rev. Biophys. Biomol. Struct. 1998, 27, 503-528.
56. Stephens, L. R.; Downes, C. P. Product-precursor relationship amongst inositol polyphosphates. Incorporation of [32P]Pi into myo-inositol 1,3,4,6-tetrakisphosphate, myo-inositol 1,3,4,5-tetrakisphosphate, myo-inositol 3,4,5,6-tetrakisphosphate and myoinositol 1,3,4,5,6-pentakisphosphate in intact avian erythrocytes. Biochem. J. 1990, 265, 435-452.
57. Jefferson, A. B.; Auethavekiat, V.; Pot, D. A.; Williams, L. T.; Majerus, Ph. W. Signaling Inositol Polyphosphate-5-phosphatase-Characterization of activity and effect of GRB2 association. J. Biol. Chem. 1997, 272, 5983-5988.
58. Sirén, M. U.S. Patent No. 4,851,560.
59. Savoje, J. Y.; Brassard, P. O. Sur les présumés cis-dihalogénures de quinones. Can. J. Chem. 1966, 44, 2867-2872.
60. Secen, H.; Maras, A.; Suetbeyaz, Y.; Balci, M. A Novel Synthesis of Conduritol-C and Conduritol-E via p-Benzoquinone. Synth. Commun. 1992, 22, 2613-2619
61. Koreeda, M.; Yoshihara, M. The Absolute Configuration of Anti-Benzene and Anti-Naphthalene 1,2:3,4-Dioxides. J. Chem. Soc., Chem. Commun. 1981, 974-976.
62. 4 (inositol 1,3,4,5-tetrakisphosphate) receptor from brain by an anti-peptide antiserum. FEBS Lett. 1995, 370, 236-240.