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A comparative study of quinolinium dichromate oxidation with hydrophobic dependence amino acids. A kinetic and mechanistic approach

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Abstract

A detailed study of kinetics is required to predict the susceptibility of amino acid residues towards metal-catalyzed oxidation. The effect of quinolinium dichromate on the oxidation of a set of amino acid residues with different hydrophobicity in HClO4 medium at 25 °C has been fairly studied. The kinetics of the reaction was followed spectrophotometrically at λmax = 440 nm. The reaction has unit dependence on each of the substrates, quinolinum dichromate and acid concentrations. The effect of dielectric constant of the medium on the rate was studied. The induced polymerization of acrylonitrile was observed. The oxidation products were isolated and characterized. Dependence of reaction rate on temperature has been studied and activation parameters were computed. A mechanism consistent with the observed results has been proposed. Of the four amino acid residues, proline is oxidized at a faster rate than all other amino acids. This may be due to the hydrophobic induced oxidation. Therefore, the overall order of amino acid sensitivity to oxidation was found to be Pro > Thr > Ser > Lys.

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References

  1. 1.

    Berlett B.S. and Stadtman E.R. (1997). J. Biol. Chem. 272: 20313

  2. 2.

    Stadtman E.R. (1992). Science 257: 1220

  3. 3.

    Hawkins C.L. and Davies M.J. (2001). Biochim. Biophys. Acta 196: 1504

  4. 4.

    Sumner E.R., Shanmuganathan A., Sideri T.C., Willetts S.A., Houghton J.E. and Avery S.V. (2005). Microbiology 151: 1939

  5. 5.

    Nalwaya N., Jain A. and Hiran B.L. (2004). Kinet. Catalysis 45: 345

  6. 6.

    Mansour M.A. (2002). Transition Met. Chem. 27: 818

  7. 7.

    Chimatadar S.A., Koujalagi S.B. and Nandibewoor S.T. (2002). Transition Met. Chem. 27: 704

  8. 8.

    Kulkarni R.M., Bilehal D.C. and Nandibewoor S.T. (2004). Anal. Sci. 20: 743

  9. 9.

    Sadeghi M.M., Baltork I.M., Azarm M. and Mazidi M.R. (2001). Synth. Commun. 31: 435

  10. 10.

    Balasubramanian K. and Prathibha V. (1986). Indian J. Chem. 25B: 326

  11. 11.

    E.J. Corey, E.P. Barrette and P. Magriotis, Tetrahedron Lett. (1985) 5855

  12. 12.

    Abiraj K., Baba A.R., Srinivasa G.R. and Gowda D.C. (2006). J. Phys. Org. Chem. 19: 68

  13. 13.

    Srinivasa G.R., Abiraj K., Baba A.R. and Gowda D.C. (2006). Int. J. Chem. Kinet. 38: 115

  14. 14.

    Gowda D.C., Gowda B.K.K. and Rangappa K.S. (2001). J. Phys. Org. Chem. 14: 716

  15. 15.

    Mangalan G. and Meenakshisundaram S. (1991). J. Indian Chem. Soc. 68: 77

  16. 16.

    K.B. Wiberg (1965). Oxidations in Organic Chemistry. Academic Press, New York

  17. 17.

    Ganeshan T.K., Rajgopal S. and Bharathy J.B. (2000). Tetrahedron 56: 5885

  18. 18.

    Stearns D.M. and Wetterhahn K.E. (1994). Chem. Res. Toxicol. 7: 219

  19. 19.

    Codd R., Lay P.A. and Levina A. (1997). Inorg. Chem. 36: 5440

  20. 20.

    Amis E.S. (1966). Solvent Effects on Reaction Rates and Mechanisms. Academic Press, New York

  21. 21.

    Wiberg K.B. (1955). Chem. Rev. 55: 713

  22. 22.

    Collins C.J. and Bowmann N.S. (1970). Isotopic Effects in Chemical Reactions. Van Nostrand-Reinhold, New York, 267

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Correspondence to Channe D. Gowda.

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Ravishankar, S.L., Baba, R.A., Rangaswamy et al. A comparative study of quinolinium dichromate oxidation with hydrophobic dependence amino acids. A kinetic and mechanistic approach. Transition Met Chem 32, 407–410 (2007). https://doi.org/10.1007/s11243-007-0192-8

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Keywords

  • Boiling Tube
  • Chromium Trioxide
  • Chromic Acid Oxidation
  • Total Volume Constant
  • Amino Acid Sensitivity