Organic biomolecules bind to phosphate through borate linkages in aqueous solutions
Solutions of salicyclic, ascorbic, and citric acids were reacted with boric acid, followed by NaH2PO4. The products, triphosphateborate ester of salicylic acid (1), orthosphateborate ester of ascorbic acid (2), triphosphateborate ester of ascorbic acid (3), and orthosphateborate ester of citric acid (4), were flash precipitated with cold acetone and characterised by microanalysis, thermal analysis, FT-IR, Raman, 11B NMR, 31P MAS NMR, and mass spectroscopic techniques. Analytical results indicated the presence of --C--O--B--O--P-- linkages with the attached phosphate groups varying between orthophosphate and triphosphate, depending on the starting material. The biomolecules studied in this work may serve as models in the B--P-organic system and the results would provide a possible contribution to boron prebiotic chemistry.
Organic biomolecules bind to phosphate through borate linkages in aqueous solutions
Solutions of salicyclic, ascorbic, and citric acids were reacted with boric acid, followed by NaH2PO4. The products, triphosphateborate ester of salicylic acid (1), orthosphateborate ester of ascorbic acid (2), triphosphateborate ester of ascorbic acid (3), and orthosphateborate ester of citric acid (4), were flash precipitated with cold acetone and characterised by microanalysis, thermal analysis, FT-IR, Raman, 11B NMR, 31P MAS NMR, and mass spectroscopic techniques. Analytical results indicated the presence of --C--O--B--O--P-- linkages with the attached phosphate groups varying between orthophosphate and triphosphate, depending on the starting material. The biomolecules studied in this work may serve as models in the B--P-organic system and the results would provide a possible contribution to boron prebiotic chemistry.
___
- Cairns-Smith, A. G. Seven Clues to the Origin of Life, Cambridge University Press: Cambridge, UK, 1985.
- Fitz, D.; Reiner, H.; Rode, B. M. Pure Appl. Chem. 2007, 79, 2101–2117.
- Arrhenius, G.; Sales, B.; Mojzsis, S.; Lee, T. J. Theor. Biol. 1987, 187, 503–522.
- Arrhenius, G. O. Helv. Chim. Acta 2003, 86, 1569–1586.
- Schwartz, A. W. Phil. Trans. R. Soc. B. 2006, 361, 1743–1749.
- Ricardo, A.; Carrigan, M. A.; Olcott, A. N.; Benner, S. A. Science 2004, 303, 196.
- Amaral, A. F.; Marques, M. M.; da Silva, J. A. L.; da Silva, J. J. R. F. New J. Chem. 2008, 32, 2043–2049.
- Scorei, R. Orig. Life Evol. Biosph. 2012, 42, 3–17.
- Prieur, B. E. C. R. Acad. Sci. Ser. IIC Chem. 2001, 4, 667–670.
- Scorei, R.; Cimpoiasu, V. M. Orig. Life Evol. Biosph. 2006, 36, 1–11.
- K¨ose, D. A.; Z¨umreoglu-Karan, B. New J. Chem. 2009, 33, 1874–1881.
- Saladino, R.; Barontini, M.; Cossetti, C.; Di Mauro, E.; Crestini, C. Orig. Life Evol. Biosph. 2011, 41, 317–330.
- Holm, N. G.; Dumont, M.; Ivarsson, M.; Konn, C. Geochem. T. 2006, 7, 1–7.
- Nikonov, G. N.; Balyeva, A. S. Russ. Chem. Rev. 1992, 61, 335–351.
- Hauf, C.; Kniep, E. R. Z. Kristallogr. 1996, 211, 705–706.
- Boy, I.; Hauf, C.; Kniep, R. Z. Naturforsch B 1998, 53, 631–633.
- Bontchev, R. P.; Sevov, S. C. Inorg. Chem. 1996, 35, 6910–6911.
- Li, M. R.; Mao, S. Y.; Huang, Y. X.; Mi, J. X.; Wei, Z. B.; Zhao, J. T.; Kniep R. Z. Krist. - New Cryst. St. 2002, 217, 165–166.
- K¨ose, D. A.; Z¨umreoglu-Karan, B.; H¨okelek, T.; Sahin, E. Inorg. Chim Acta 2010, 363, 4031–4037.
- K¨ose, D. A.; Z¨umreoglu-Karan, B.; H¨okelek, T. Inorg. Chim. Acta 2011, 375, 236–241.
- Chvertkina, L. V.; Khoklov, P. S.; Mironov, V. F. Russ. Chem. Rev. 1992, 61, 1009–1021.
- Van Duin, M.; Peters, J. A.; Kieboom, A. P. G.; Van Bekkum, H. Tetrahedron 1984, 40, 2901–2911.
- Kulaev, I. S.; Vagabov, V. M.; Kulakovskaya, T. V. The Biochemistry of Inorganic Polyphosphates, Wiley: New York, NY, USA, 2004, pp. 3–14.
- Kirkpatrick, R. J.; Brow, R. K. Solid State Nucl. Mag. Res. 1995, 5, 9–21.
- Wiench, J. M.; Pruski, M.; Tischendorf, B.; Otaigbe, J. U.; Sales, B. C. J. Non-Cryst. Solids 2000, 263, 101–110.
- Carta, D.; Qiu, D.; Guerry, I.; Ahmed, P.; Abou Neel, E. A.; Knowles, J. C.; Smith, M. E.; Newport, R. J. J. Non-Cryst Solids 2008, 354, 3671–3677.
- Peak, D.; Luther, G. W.; Sparks, D. L. Geochim. Cosmochim. Acta 2003, 67, 2551–2560.
- Efimov, A. M. J. Non-Cryst. Solids 1997, 209, 209–226.
- Saranti, A.; Koutselas, I.; Karakassides, M. A. J. Non-Cryst. Solids 2006, 352, 390–398.
- Oertel, R. P. Inorg. Chem. 1972, 11, 544–549.
- Gaylord, S.; Tincher, B.; Petit, L.; Richardson, K. Mater. Res. Bull. 2009, 44, 1031–1035.
- Kim, N. J.; Im, S. H.; Kim, D. H.; Yoon, D. K.; Ryu, B. K. Electron. Mater. Lett. 2010, 6, 103–106.
- Turner, B. L.; Mahieu, N.; Condron, L. M. Soil Sci. Soc. Am. J. 2003, 67, 497–510.
- Brow, R. K. J. Non-Cryst. Solids 2000, 263 & 264, 1–28.
- Munoz, F.; Montagne, L.; Pascual, L.; Duran, A. J. Non-Cryst. Solids 2009, 355, 2571–2577.
- Shah, K. V.; Goswami, M.; Deot, M. N.; Sarkar, A.; Manikandan, S.; Shrikhande, V. K.; Kothiyal, G. P. Bull. Mater. Sci. 2006, 29, 43–48.
- Grimmer, A. R.; M¨uller, D.; G¨ozel, G.; Kniep, R. Fresen. J. Anal. Chem. 1997, 357, 485–488.
- Elbers, S.; Strojek, W.; Koudelka, L.; Eckert, H. Solid State Nucl. Magn. Reson. 2005, 27, 65–76.
- Beckett, M. A.; Rugen-Hankey, M. P.; Varma, K. S. J. Sol-Gel Sci. Techn. 2006, 39, 95–101.
- Kennedy, J. D. In: Mason J. (ed) Multinuclear NMR, Plenum: New York, NY, USA, 1987, 221-253.
- Bishop, M.; Shahid, N.; Yang, J.; Barron, A. R. Dalton Trans. 2004, 7, 2621–2634.
- Tossell, J. A. Geochim. Cosmochim. Acta 2006, 70, 5089–5103.
- K¨ose, D. A.; Z¨umreoglu-Karan, B. Chem. Pap. 2012, 66, 54–60.
- Michelmore, A.; Gong, W.; Jenkins, P.; Ralston, J. Phys. Chem. Chem. Phys. 2000, 2, 2985–2992.
- Gong, W. Int. J. Miner. Process. 2001, 63, 147–165.
- Vyatchina, V. G.; Perelyaeva, L. A.; Zuev, M. G.; Mamoshin, V. L. Glass. Phys. Chem. 2003, 29, 522–525.
- De Gelder, J.; De Gussem, K.; Vandenabeele, P.; Moens, L.; J. Raman Spectrosc. 2007, 38, 1133–1147.
- Matsunaga, T.; Nagata, T. Anal. Sci. 1995, 11, 889–892.
- Shao, C. Y.; Matsuoka, S.; Miyazaki, Y.; Yoshimura, K. Anal. Sci. 2001, 17, i1475–i1478.
- Beckett, M. A.; Bland, C. C.; Varma, K. S. Polyhedron 2008, 27, 2226–2230.
- Dawber, J. G.; Green, S. I. E. J. Chem. Soc. Faraday Trans. I 1986, 82, 3407–3413.
- Dawber, J. G. J. Chem. Soc. Faraday Trans. I 1987, 83, 771–777.
- Dawber, J. G.; Green, S. I. E.; Dawber, J. C.; Gabrail, S. J. Chem. Soc. Faraday Trans. I 1988, 84, 41–45.
- K¨ose, D. A. Dissertation, Hacettepe University, Turkey, 2008.
- Zviedre, I. I.; Belyakov, S. V. J. Struct. Chem. 2009, 50, 114–119.
- Zviedre, I. I.; Belyakov, S. V. Russ. J. Inorg. Chem. 2009, 54, 1390–1395.
- Pasek, M. A. P. Natl. Acad. Sci. USA 2008, 105, 853–858.
- Weicher, F. H. Standard Methods of Chemical Analysis, Part B, 6th edn. Van Nostrand: New York, NY, USA, 1963, pp. 2406–2407.