Enzyme-free synthesis of natural phospholipids in water (original) (raw)

References

  1. Jackowski, S, Cronan, J. E. Jr & Rock, C. O. Biochemistry of Lipids, Lipoproteins and Membranes Vol. 20, 80–81 (Elsevier, 1991).
  2. Lands, W. E. M. Metabolism of glycerolipides: a comparison of lecithin and triglyceride synthesis. J. Biol. Chem. 231, 883–888 (1958).
    CAS PubMed Google Scholar
  3. Schmidli, P. K., Schurtenberger, P. & Luisi, P. L. Liposome-mediated enzymatic synthesis of phosphatidylcholine as an approach to self-replicating liposomes. J. Am. Chem. Soc. 113, 8127–8130 (1991).
    Article CAS Google Scholar
  4. Deamer, D. W. & Boatman, D. E. An enzymatically driven membrane reconstitution from solubilized components. J. Cell Biol. 84, 461–467 (1980).
    Article CAS Google Scholar
  5. Morris-Natschke, S. L. et al. Synthesis of phosphocholine and quaternary amine ether lipids and evaluation of in vitro antineoplastic activity. J. Med. Chem. 36, 2018–2025 (1993).
    Article CAS Google Scholar
  6. Harayama, T. et al. Lysophospholipid acyltransferases mediate phosphatidylcholine diversification to achieve the physical properties required in vivo. Cell Metabol. 20, 295–305 (2014).
    Article CAS Google Scholar
  7. Hargreaves, W. R., Mulvihill, S. J. & Deamer, D. W. Synthesis of phospholipids and membranes in prebiotic conditions. Nature 266, 78–80 (1977).
    Article CAS Google Scholar
  8. Fernandez-Garcia, C. & Powner, M. W. Selective acylation of nucleosides, nucleotides, and glycerol-3-phosphocholine in water. Synlett 28, 78–83 (2017).
    CAS Google Scholar
  9. Bonfio, C. et al. Length-selective synthesis of acylglycerol-phosphates through energy-dissipative cycling. J. Am. Chem. Soc. 141, 3934–3939 (2019).
    Article CAS Google Scholar
  10. Szostak, J. W., Bartel, D. P. & Luisi, P. L. Synthesizing life. Nature 409, 387–390 (2001).
    Article CAS Google Scholar
  11. Budin, I. & Szostak, J. W. Physical effects underlying the transition from primitive to modern cell membranes. Proc. Natl Acad. Sci. USA 108, 5249–5254 (2011).
    Article CAS Google Scholar
  12. de Ouve, C. The beginnings of life on earth. American Scientist 83, 428–437 (1995).
    Google Scholar
  13. Ejsinga, C. S. et al. Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry. Proc. Natl Acad. Sci. USA 106, 2136–2141 (2009).
    Article Google Scholar
  14. Brea, R. J., Cole, C. M. & Devaraj, N. K. In situ vesicle formation by native chemical ligation. Angew. Chem. Int. Ed. 53, 14102–14105 (2014).
    Article CAS Google Scholar
  15. Bender, M. L. Mechanisms of catalysis of nucleophilic reactions of carboxylic acid derivatives. Chem. Rev. 60, 53–113 (1960).
    Article CAS Google Scholar
  16. McClelland, R. A. & Santry, L. J. Reactivity of tetrahedral intermediates. Acc. Chem. Res. 16, 394–399 (1983).
    Article CAS Google Scholar
  17. Raynal, M., Ballester, P., Vidal-Ferran, A. & van Leeuwen, P. W. N. M. Supramolecular catalysis. Part 1: non-covalent interactions as a tool for building and modifying homogeneous catalysts. Chem. Soc. Rev. 43, 1660–1733 (2014).
    Article CAS Google Scholar
  18. Steinman, G. & Cole, M. N. Synthesis of biologically pertinent peptides under possible primordial conditions. Proc. Natl Acad. Sci. USA 58, 735–742 (1967).
    Article CAS Google Scholar
  19. Toparlak, D., Karki, M., Egas Ortuno, V., Krishnamurthy, R. & Mansy, S. S. Cyclophospholipids increase protocellular stability to metal ions. Small 16, 1903381 (2019).
  20. Rao, M., Eichberg, J. & Oró, J. Synthesis of phosphatidylcholine under possible primitive Earth conditions. J. Mol. Evol. 18, 196–202 (1982).
    Article CAS Google Scholar
  21. Frisch, M. J. et al. Gaussian 09, Revision A.02 (Gaussian Inc, 2016).
  22. Marenich, A. V., Cramer, C. J. & Truhlar, D. G. Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. J. Phys. Chem. B 113, 6378–6396 (2009).
    Article CAS Google Scholar
  23. Delory, D. E. & King, E. J. A sodium carbonate-bicarbonate buffer for alkaline phosphatases. Biochem. J. 39, 245 (1945).
    Article CAS Google Scholar
  24. Kempe, S. & Degens, E. T. An early soda ocean? Chem. Geol. 53, 95–108 (1985).
    Article CAS Google Scholar
  25. Martin, W. & Russell, M. J. On the origin of biochemistry at an alkaline hydrothermal vent. Phil. Trans. R. Soc. B 362, 1887–1925 (2007).
    Article CAS Google Scholar
  26. Perkins, W. R. et al. Role of lipid polymorphism in pulmonary surfactant. Science 273, 330–332 (1996).
    Article CAS Google Scholar
  27. Athenstaedt, K. & Daum, G. Phosphatidic acid, a key intermediate in lipid metabolism. Eur. J. Biochem. 266, 1–16 (1999).
    Article CAS Google Scholar
  28. Chen, I. A. & Szostak, J. W. Membrane growth can generate a transmembrane pH gradient in fatty acid vesicles. Proc. Natl Acad. Sci. USA 101, 7965–7970 (2004).
    Article CAS Google Scholar
  29. Morese, J. W. & Mackenzie, F. T. Hadean ocean carbonate geochemistry. Aquat. Geochem. 4, 301–319 (1998).
    Article Google Scholar
  30. Macleod, G., McKeown, C., Hall, A. J. & Russell, M. J. Hydrothermal and oceanic pH conditions of possible relevance to the origin of life. Orig. Life Evol. Biospheres 24, 19–41 (1994).
    Article CAS Google Scholar

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