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Structure and Nomenclature of Inositol Phosphates, Phosphoinositides, and Glycosylphosphatidylinositols

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Part of the Subcellular Biochemistry book series (SCBI,volume 39)

6. Conclusions

Inositol is a deceptively simple molecule. On closer study, a number of sophisticated stereochemical, prochiral, chiral, and conformational issues associated with inositols and their derivatives become evident. Inositols, in particular myo-inositol, play a central role in cellular metabolism. An array of complicated molecules that incorporate the inositol moiety are found in nature. Structural heterogeneity of inositol derivatives is compounded by the presence of stereo- and regioisomers of the inositol unit. Because of the large number of isomeric inositols and their derivatives present in nature, a detailed understanding of the structural, stereochemical, and nomenclature issues involving inositol and its derivatives is essential to investigate biological aspects. A discussion of the stereochemical, conformational, prochiral, chiral, and nomenclature issues associated with inositols and the structural variety of insoitol derivatives is presented in this chapter.

Keywords

  • Phytic Acid
  • Inositol Phosphate
  • Conformational Isomer
  • Inositol Hexakisphosphate
  • Meso Compound

These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  • Agranoff, B.W., 1978, Textbook errors: Cyclitol confusion. Trends Biochem. Sci. 3: N283–N285.

    CrossRef  CAS  Google Scholar 

  • Agranoff, B.W., Murthy, P.P.N., and Sequin, E.B., 1983, Thrombin-induced phosphodiesteratic cleavage of phosphatidylinositol bisphosphate in human platelets. J. Biol. Chem. 258:2076–2078.

    PubMed  CAS  Google Scholar 

  • Ballou, C.E., and Pizer, L.I., 1960, The absolute configuration of the myo-inositol 1-phosphates and a confirmation of the bornesitol configuration. J. Am. Chem. Soc. 82: 3333–3335.

    CrossRef  CAS  Google Scholar 

  • Barrientos, L.G., and Murthy, P.P.N., 1996, Conformational studies of myo-inositol phosphates. Carbohydr. Res. 296: 39–54.

    CrossRef  PubMed  CAS  Google Scholar 

  • Bauman, A.T., Chateauneuf, G.M., Boyd, B.R., Brown, R.E., and Murthy, P.P.N., 1999, Conformational inversion processes in phytic acid: NMR spectroscopic and molecular modeling studies. Tetrahedron Lett. 40: 4489–4492.

    CrossRef  CAS  Google Scholar 

  • Bernfield, M., Gotte, M., Park, P.W., Reizes, O., Fitzgerald, M.L., Lincecumj, J., and Zako, M., 1999, Functions of cell surface heparan sulfate proteoglycans. Annu. Rev. Biochem. 68:729–777.

    CrossRef  PubMed  CAS  Google Scholar 

  • Blank, G.E., Pletcher, J., and Sax, M., 1971, The structure of myo-inositol hexaphosphate dodecasodium salt octatriacontahydrate: A single crystal X-ray analysis. 44: 319–325.

    CAS  Google Scholar 

  • Carey, F.A., and Sundberg, R.J., 2000, Advanced Organic Chemistry, Part A, Structure and Mechanism, 4th ed. Kluwer Academic/Plenum Publishers, New York, pp. 123–185.

    Google Scholar 

  • Deitz, M.P., and Albersheim, P., 1965, The enzymic phosphorylation of myo-inositol. Biochem. Biophys. Res. Commun. 19: 598–602.

    CrossRef  Google Scholar 

  • Folch, J., and Woolley, D.W., 1942, Inositol, a constituent of a brain phosphatide. J. Biol. Chem. 142: 963–964.

    CAS  Google Scholar 

  • Hokin, M.R., and Hokin, L.E., 1953, Enzyme secretion and the incorporation of P32 into phospholipides of pancreatic slices. J. Biol. Chem. 203: 967–977.

    PubMed  CAS  Google Scholar 

  • Irvine, R.F., and Schell, M.J., 2001, Back in the water: The return of the inositol phosphates. Nat. Rev. Mol. Cell. Biol. 2: 327–338.

    CrossRef  PubMed  CAS  Google Scholar 

  • Isbrandt, L.R., and Oertei, R.P., 1980, Conformational states of myo-inositol hexakis(phosphate)in aqueous solution. A 13C NMR, 31P NMR, and Raman spectroscopic investigation. J. Am. Chem. Soc. 102: 3144–3148.

    CrossRef  CAS  Google Scholar 

  • IUB Nomenclature Committee, 1989, Numbering of atoms in myo-inositol. Biochem. J. 258: 1–2.

    Google Scholar 

  • IUPAC Commission on the Nomenclature of Organic Chemistry and IUPAC-IUB Commission on Biochemical Nomenclature, 1976, Nomenclature of cyclitols. Biochem. J. 153: 23–31.

    Google Scholar 

  • Kunze, M., Riedel, J., Lange, U., Hurwitz, R., and Tischner, R., 1997, Evidence for the presence of GPI-anchored PM-NR in leaves of Beta vulgaris and from PM-NR in barley leaves. Plant Physiol. Biochem. 35: 507–512.

    CAS  Google Scholar 

  • Larner, J., Huang, L.C., Schwartz, C.F.W., Oswald, A.S., Shen, T.-Y., Kinter, M., Tang, G., and Zeller, K., 1988, Rat liver insulin mediator which stimulates pyruvate dehydrogenase phosphatase contains galatosamine and D-chiroinositol. Biochem. Biophys. Res. Commun. 151: 1416–1426.

    CrossRef  PubMed  CAS  Google Scholar 

  • Lasztity, R., and Lasztity, L., 1990, Phytic acid in cereal technology. Adv. Cereal Sci. Technol. 10:309–371.

    CAS  Google Scholar 

  • Loewus, F.A., 1990a, Inositol biosynthesis, metabolism: Precursor role and breakdown. In: Morre, D.J., Boss, W.F., and Loewus, F.A. (eds.), Inositol Metabolism in Plants. Wiley-Liss, New York, NY, pp. 13–19.

    Google Scholar 

  • Loewus, F.A., 1990b, Inositol metabolism: Precursor role and breakdown. In: Morre, D.J., Boss, W.F., and Loewus, F.A. (eds.), Inositol Metabolism in Plants. Wiley-Liss, New York, pp. 21–45.

    Google Scholar 

  • Loewus, F.A., and Murthy, P.P.N., 2000, myo-Inositol metabolism in plants. Plant Sci. 150: 1–19.

    CrossRef  CAS  Google Scholar 

  • Loewus, M.W., Sasaki, K., Laevitt, A.L., Munsell, L., Sherman, W.R., and Loewus, F.A., 1982, The enantiomeric form of myo-inositol-1-phosphate produced by myo-inositol 1-phosphate synthase and myo-inositol kinase in higher plants. Plant Physiol. 70: 1661–1663.

    CrossRef  PubMed  CAS  Google Scholar 

  • Low, M.G., 1989, The glycosyl-phosphatidylinositol anchor of membrane proteins. Biochim. Biophys. Acta 988: 427–454.

    PubMed  CAS  Google Scholar 

  • Low, M.G., 2000, Glycosylphosphatidylinositol-anchored proteins and their phospholipases. In: Cockcroft, S. (ed.), Frontiers in Molecular Biology, Vol. 27, Biology of Phosphoinositides. Oxford University Press, New York, pp. 211–238.

    Google Scholar 

  • Low, M.G., and Saltiel, A.R., 1988, Structural and functional roles of glycosylphosphatidylinositol in membranes. Science 239: 268–275.

    PubMed  CAS  Google Scholar 

  • Mato, J.M., Kelly, K.L., Abler, A., and Jarett, L. 1987, Identification of a novel insulin-sensitive glycophospholipid from H35 hepatoma cells. J. Biol. Chem. 262: 2131–2137.

    PubMed  CAS  Google Scholar 

  • Murthy, P.P.N., 1996, Metabolism of inositol phosphates in plants. In: Biswas, B.B. and Biswas, S. (eds.), Inositol Phosphates, Phosphoinositides, and Signal Transduction, Subcellular Biochemistry Series, Vol. 26, Plenum Press, New York, pp. 227–255.

    Google Scholar 

  • Narasimhan, B., Pliska-Matyshak, G., Kinnard, R., Carstensen, S., Ritter, M.A., von Weymarn L., and Murthy, P.P.N., 1997, Novel phosphoinositides in barley aleurone cells, additional evidence for the presence of phosphatidyl-scyllo-inositol. Plant Physiol. 113: 1385–1393.

    PubMed  CAS  Google Scholar 

  • Pak, Y., and Larner, J., 1992, Identification and characterization of chiroinositol-containing phospholipids form bovine liver. Biochem. Biophys. Res. Commun. 184: 1042–1047.

    CrossRef  PubMed  CAS  Google Scholar 

  • Parthasarathy, R., and Eisenberg, F., Jr., 1986, The inositol phospholipids: A stereochemical view of biological activity. Biochem. J. 235: 313–322.

    PubMed  CAS  Google Scholar 

  • Parthasarathy, R., and Eisenberg, F., Jr., 1990, Biochemistry, stereochemistry, and nomenclature of the inositol phosphates, In: Reitz, A.B. (ed.), Inositol Phosphates and Derivatives: Synthesis, Biochemistry, and Therapeutic Potential. ACS Symposium Series 463. American Chemical Society, Washington, DC, pp. 1–19.

    Google Scholar 

  • Posternak, T., 1965, The Cyclitols. Holden-Day, Inc., Publishers, San Francisco, CA, pp. 7–48.

    Google Scholar 

  • Saltiel, A. R., 1996, Structural and functional roles of glycosylphosphoinositides. In: Biswas, B.B. and Biswas, S. (eds.), Inositol Phosphates, Phosphoinositides, and Signal Transduction, Subcellular Biochemistry Series, Vol. 26. Plenum Press, New York, pp. 165–185.

    Google Scholar 

  • Shears, S.B., 1998, The versatility of inositol phosphates as cellular signals. Biochim. Biophys. Acta 1436: 49–67.

    PubMed  CAS  Google Scholar 

  • Shears, S.B., 2000, Inositol pentakis-and hexakisphosphate metabolism adds versatility to the actions of inositol polyphosphates novel effects on ion channels and protein traffic. In: Biswas, B.B. and Biswas, S. (eds.), Inositol Phosphates, Phosphoinositides, and Signal Transduction, Subcellular Biochemistry Series, Vol. 26. Plenum Press, New York, pp. 187–226.

    Google Scholar 

  • Shears, S.B., 2001, Assessing the omnipotence of inositol hexakisphosphate. Cell Signal. 13: 151–158.

    CrossRef  PubMed  CAS  Google Scholar 

  • Shears, S.B., 2004, How versatile are inositol phosphate kinases? Biochem. J. 377: 265–280.

    CrossRef  PubMed  CAS  Google Scholar 

  • Stephens, L., McGregor, A., and Hawkins, P., 2000, Phosphoinositide 3-kinases: Regulation by cell-surface receptors and function of 3-phosphorylated lipids. In: S. Cockcroft (ed.), Frontiers in Molecular Biology, Vol. 27, Biology of phosphoinositides. Oxford University Press, New York, pp. 32–108.

    Google Scholar 

  • Stöhr, C., Schuler, F., and Tischner, R., 1995, Glycosyl-phosphatidylinositol-anchored proteins exist in the plasma membranes of Chlorella Saccharophila (Kruger) Nadson: Plasmamembrane-bound nitrate reductase as an example. Planta 196: 284–287.

    CrossRef  Google Scholar 

  • Streb, H., Irvine, R.F., Berridge, M.J., and Schulz, I., 1983, Release of Ca2+ from a nonmitochondrial intracellular store in pancreatic acinar cells by inositol-1,4,5-trisphosphate. Nature 306: 67–69.

    CrossRef  PubMed  CAS  Google Scholar 

  • Toker, A., 2002, Phosphoinositides and signal transduction. Cell. Mol. Life Sci. 59: 761–779.

    CrossRef  PubMed  CAS  Google Scholar 

  • Toker, A., and Cantley, L.C., 1997, Signalling through the lipid products of phosphoinositide-3-OH kinase. Nature. 387: 673–676.

    CrossRef  PubMed  CAS  Google Scholar 

  • Vanhaesebroek, B., Leevers, S., Ahmadi, K., Timms, J., Katso, R., Driscoll, P.C., Woscholski, R., Parker, P.J., and Waterfield, M.D., 2001, Synthesis and function of 3-phosphorylated inositol lipids. Annu. Rev. Biochem. 70: 535–602.

    CrossRef  Google Scholar 

  • Volkmann, C.J., Chateauneuf, G.M., Pradhan, J., Bauman, A.T., Brown, R.E., and Murthy, P.P.N., 2002, Conformational flexibility of inositol phosphates: Influence of structural characteristics. Tetrahedron Lett. 43: 4853–4856.

    CrossRef  CAS  Google Scholar 

  • Whitman, M., Downes, C.P., Keeler, M., Keeler, T., and Cantley, L.C., 1988, Type-1 phosphatidylinostiol kinase makes a novel inositol phospholipid, phosphatidylinostiol-3-phosphate. Nature 332: 644–646.

    CrossRef  PubMed  CAS  Google Scholar 

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Murthy, P.P.N. (2006). Structure and Nomenclature of Inositol Phosphates, Phosphoinositides, and Glycosylphosphatidylinositols. In: Majumder, A.L., Biswas, B.B. (eds) Biology of Inositols and Phosphoinositides. Subcellular Biochemistry, vol 39. Springer, Boston, MA . https://doi.org/10.1007/0-387-27600-9_1

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