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Reactions of glutaraldehyde with dipolar ions of amino acids and proteins

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Abstract

The review covers studies of the reactions of glutaraldehyde with dipolar ions of amino acids and proteins in neutral aqueous solutions. The formation of imines and the accompanying aldol condensation of glutaraldehyde are acid-catalyzed reactions.

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References

  1. Immobilizovannye Fermenty. Sovremennoe Sostoyanie i Perspektivy [Immobilized Enzymes. Current State and Prospects], Ed. I. V. Berezin, V. K. Antonov, K. Martinek, izd-vo MGU, Moscow, 1976, vol. 1, 207 (in Russian).

    Google Scholar 

  2. Immobilized Enzymes and Cells, part D in Methods Enzymol., Ed. K. Mosbach, Acad. Press, New York, 1986, Vol. 137, 443.

    Google Scholar 

  3. S. V. Kol’tsova, Bioorgan. Khim., 1995, 21, 408 [Russ. J. Bioorg. Chem. (Engl. Transl.) 1995, 21, No. 5].

    Google Scholar 

  4. N. P. Kuznetsova, L. R. Gudkin, R. N. Mishaeva, E. A. Berezetskaya, M. E. Vylegzhanina, T. E. Sukhanova, E. F. Panarin, Prikl. Biokhim. Mikrobiol., 2010, 46, 237 [Appl. Biochem. Microbiol. (Engl. Transl.), 2010, 46, 221].

    CAS  Google Scholar 

  5. R. N. Mishaeva, L. R. Gudkin, N. P. Kuznetsova, Prikl. Biokhim. Mikrobiol., 2006, 42, 404 [Appl. Biochem. Microbiol. (Engl. Transl.), 2006, 42, 354].

    CAS  Google Scholar 

  6. N. P. Kuznetsova, L. R. Gudkin, R. N. Mishaeva, E. F. Panarin, I. M. Bystrova, E. A. Selivanov, Dokl. Akad. Nauk, 2002, 386, 267 [Dokl. Biochem. Biophys. (Engl. Transl.), 2002, 386, 257].

    Google Scholar 

  7. N. R. Kil’deeva, P. A. Perminov, L. V. Vladimirov, V. V. Novikov, S. N. Mikhailov, Bioorgan. Khim., 2009, 35, 397 [Russ. J. Bioorg. Chem. (Engl. Transl.), 2009, 35, 360].

    Google Scholar 

  8. T. N. Yudanova, I. F. Skokova, L. S. Gal’braikh, Khim. Volokno, 2000, No. 6, 21 [Fibre Chem. (Engl. Transl.), 2000, 32, 411].

    Google Scholar 

  9. S. Margel, E. Wieses, J. Polym. Sci., Polym. Chem. Ed., 1984, 22, 145.

    Article  CAS  Google Scholar 

  10. A. Rembaum, S. Margel, Y. Levy, J. Immunol. Methods, 1979, 24, 239.

    Article  Google Scholar 

  11. M. Okubo, Y. Kondo, M. Takahashi, Colloid Polym. Sci., 1993, 271, 109.

    Article  CAS  Google Scholar 

  12. L. Holmquist, M. Lewin, J. Biochem. Biophys. Methods, 1991, 22, 321.

    Article  CAS  Google Scholar 

  13. K. Peters, F. M. Richards, Annu. Rev. Biochem., 1977, 46, 523.

    Article  CAS  Google Scholar 

  14. R. E. Feeney, G. Blankenhorn, H. B. F. Dixon, Carbonylamine Reaction in Protein Chemistry, in Adv. Protein Chem., Eds C. B. Anfinsen, J. T. Edsall, F. M. Richards, Acad. Press, New York, 1975, Vol. 29, 135.

    Google Scholar 

  15. W. P. Jencks, Catalysis in Chemistry and Enzymology, McGraw-Hill Book Comp., New Jork, 1969.

    Google Scholar 

  16. V. A. Smit, A. D. Dil’man, Osnovy Sovremennogo Organicheskogo Sinteza [Fundamentals of the Modern Organic Synthesis], BINOM, Moscow, 2012, p. 171 (a); 203 (b) (in Russian).

    Google Scholar 

  17. O. A. Reutov, A. L. Kurts, K. P. Butin, Organicheskaya Khimiya [Organic Chemistry], BINOM, Moscow, 2010, Part 3, p. 23 (in Russian).

    Google Scholar 

  18. K. Ya. Burshtein, Yu. I. Khurgin, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1975, 24, 2253 [K. Ya. Burshtein, Yu. I. Khurgin, Izv. Akad. Nauk SSSR. Ser. Khim., 1975, 2365].

    Article  Google Scholar 

  19. K. Ya. Burshtein, Yu. I. Khurgin, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1985, 34, 971 [K. Ya. Burshtein, A. N. Isaev, Izv. Akad. Nauk SSSR. Ser. Khim., 1985, 1066].

    Article  Google Scholar 

  20. K. Ya. Burshtein, Yu. I. Khurgin, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1977, 26, 1369 [K. Ya. Burshtein, Yu. I. Khurgin, Izv. Akad. Nauk SSSR. Ser. Khim., 1977, 1490]

    Article  Google Scholar 

  21. K. Ya. Burshtein, Yu. I. Khurgin, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1977, 26, 1373 [K. Ya. Burshtein, Yu. I. Khurgin, Izv. Akad. Nauk SSSR. Ser. Khim., 1977, 1494].

    Article  Google Scholar 

  22. J. A. Kereselidze, T. Sh. Zarqua, T. J. Kikalishvili, E. J. Churgulia, M. S. Makaridze, Russ. Chem. Rev., 2002, 71, 993.

    Article  CAS  Google Scholar 

  23. P. Sykes, Guidebook to Mechanism in Organic Chemistry, Longman, Harlow, 1986, 416 pp.

    Google Scholar 

  24. R. Brettel, Aldehydes and Ketones, in Comprehensive Organic Chemistry, Eds D. Barton, W. D. Ollis, Pergamon Press, Oxford, 1979, Vol. 2, 1329 pp.

    Google Scholar 

  25. L. P. Hammett, Physical Organic Chemistry. Reaction Rates, Equilibria and Mechanisms, McGraw-Hill, New Jork, 1970.

    Google Scholar 

  26. S. M. Lukyanov, A. V. Koblik, Russ. Chem. Rev., 1996, 65, 1.

    Article  Google Scholar 

  27. F. M. Richards, J. R. Knowles, J. Mol. Biol., 1968, 37, 231.

    Article  CAS  Google Scholar 

  28. P. M. Hardy, A. C. Nicholls, Y. N. Rydon, Chem. Commun., 1969, 565.

    Google Scholar 

  29. E. B. Whipple, M. Ruta, J. Org. Chem., 1974, 39, 1666.

    Article  CAS  Google Scholar 

  30. A. H. Korn, S. Y. Feairheller, E. M. Filachione, J. Mol. Biol., 1972, 65, 525.

    Article  CAS  Google Scholar 

  31. P. M. Hardy, H. C. Nicholls, H. N. Rydon, J. Chem. Soc., Perkin Trans., 2, 1972, 2270.

    Google Scholar 

  32. J-i. Kawahara, T. Ohmori, T. Ohkubo, S. Hattori, M. Kawamura, Anal. Biochem., 1992, 201, 94.

    Article  CAS  Google Scholar 

  33. T. Nakagawa, K. Izawa, S. Jagi, A. Shibukawa, H. Tanaka, T. Tashima, Chem. Pharm. Bull., 1989, 37, 2463.

    Article  Google Scholar 

  34. T. Tashima, U. Kawakami, M. Harada, T. Sakata, N. Satoh, T. Nakagawa, H. Tanaka, Chem. Pharm. Bull., 1987, 35, 4169.

    Article  CAS  Google Scholar 

  35. P. Monsan, G. Puzo, H. Mazarguil, Biochemie, 1975, 57, 1281.

    Article  CAS  Google Scholar 

  36. S. Margel, A. Rembaum, Macromolecules, 1980, 13, 19.

    Article  CAS  Google Scholar 

  37. A. Rembaum, S. Margel, Br. Polym. J., 1978, 10, 275.

    Article  CAS  Google Scholar 

  38. S. Margel, J. Polym. Sci., Polym. Chem. Ed., 1984, 22, 3521.

    Article  CAS  Google Scholar 

  39. O. V. Sverdlova, Elektronnye Spektry v Organicheskoi Khimii [Electronic Spectra in Organic Chemistry], Khimiya, Leningrad, 1985, p. 98.

    Google Scholar 

  40. F. Dijk, J. A. Oosterbaan, C. E. Hulstaert, Histochemistry, 1985, 83, 573.

    Article  CAS  Google Scholar 

  41. K.-E. Rassmussen, J. Albrechtsen, Histochemistry, 1974, 38, 19.

    Article  Google Scholar 

  42. P. M. Hardy, G. J. Hughes, H. N. Rydon, J. Chem. Soc., Perkin Trans. 1, 1979, 2282.

    Google Scholar 

  43. Y. Tomimatsu, E. F. Jansen, W. Gaffield, A. C. Olson, J. Colloid. Interface Sci., 1971, 36, 51.

    Article  CAS  Google Scholar 

  44. J. H. Bowes, C. W. Cater, Biochem. Biophys. Acta, Protein Struct., 1968, 168, 341.

    Article  CAS  Google Scholar 

  45. E. F. Jansen, Y. Tomimatsu, A. C. Olson, Arch. Biochem. Biophys., 1971, 144, 394.

    Article  CAS  Google Scholar 

  46. N. F. Kazanskaya, O. A. Kost, I. V. Berezin, Bioorgan. Khim., 1975, 1, 1113 [Sov. J. Bioorg. Chem. (Engl. Transl.), 1975, 1].

    Google Scholar 

  47. D. Hopwood, Theoretical and Practical Aspects of Glutaraldehyde Fixation, in Fixation in Histochemistry, Ed. P. Stoward, Chapman Hall, London, 1973, p. 47.

    Chapter  Google Scholar 

  48. F. F. S. H. Habeeb, R. Hiramoto, Arch. Biochem. Biophys., 1968, 126, 16.

    Article  CAS  Google Scholar 

  49. N. P. Kuznetsova, G. V. Samsonov, Vysokomolekulyar. Soedin., Ser. A, 1985, 27, 2611 [Polym. Sci. USSR, Ser. A (Engl. Transl.), 1985, 27].

    CAS  Google Scholar 

  50. G. Blauer, D. Harmatz, E. Meir, M.K. Swenson, B. Zvilichovsky, Biopolymers, 1975, 14, 2587.

    Article  Google Scholar 

  51. N. P. Kuznetsova, L. R. Gudkin, G. V. Samsonov, Bioorgan. Khim., 1990, 16, 41 [Sov. J. Bioorg. Chem. (Engl. Transl.), 1990, No. 1].

    CAS  Google Scholar 

  52. J. W. Payne, Biochem. J., 1973, 135, 867.

    CAS  Google Scholar 

  53. D. Hopwood, C. R. Allen, M. McCabe, Histochem. J., 1970, 137.

    Google Scholar 

  54. N. P. Kuznetsova, S. I. Klenin, L. A. Volkova, L. R. Gudkin, G. V. Samsonov, Vysokomolekulyar. Soedin., Ser. A, 1989, 31, 1539 [Polym. Sci. USSR, Ser. A (Engl. Transl.), 1989, 31].

    CAS  Google Scholar 

  55. A. V. Glinka, A. S. Voronina, Bioorgan. Khim., 1977, 3, 1070 [Sov. J. Bioorg. Chem. (Engl. Transl.), 1977, 3].

    CAS  Google Scholar 

  56. D. Hopwood, Histochem. J., 1972, 4, 197.

    Article  Google Scholar 

  57. N. P. Kuznetsova, G. V. Samsonov, Vysokomolekulyar. Soedin., Ser. A, 1986, 28, 643 [Polym. Sci. USSR, Ser. A (Engl. Transl.), 1986, 28].

    CAS  Google Scholar 

  58. A. L. Lehnindger, Biochemistry, Worth Publ. Inc., New York, 1972.

    Google Scholar 

  59. N. R. Roe, G. Mitchel, Anal. Chem., 1951, 23, 1758.

    Article  CAS  Google Scholar 

  60. R. Fields, Biochem. J., 1971, 124, 581.

    CAS  Google Scholar 

  61. N. P. Kuznetsova, R. N. Mishaeva, L. R. Gudkin, Zh. Prikl. Khim., 1999, 72, 1171 [Russ. J. Appl. Chem. (Engl. Transl.), 1999, 72, 1236].

    CAS  Google Scholar 

  62. N. P. Kuznetsova, R. N. Mishaeva, O. A. Pisarev, L. R. Gudkin, Zh. Prikl. Khim., 2000, 73, 796 [Russ. J. Appl. Chem. (Engl. Transl.), 2000, 73, 846].

    CAS  Google Scholar 

  63. N. P. Kuznetsova, L. R. Gudkin, R. N. Mishaeva, Zh. Prikl. Khim., 2002, 75, 991 [Russ. J. Appl. Chem. (Engl. Transl.), 2002, 75, 974].

    Google Scholar 

  64. N. P. Kuznetsova, O. A. Pisarev, R. N. Mishaeva, L. R. Gudkin, Zh. Prikl. Khim., 2003, 76, 1848 [Russ. J. Appl. Chem. (Engl. Transl.), 2003, 76, 1798].

    Google Scholar 

  65. L. R. Gudkin, N. P. Kuznetsova, R. N. Mishaeva, Zh. Prikl. Khim., 1997, 70, 820 [Russ. J. Appl. Chem. (Engl. Transl.), 1997, 70, 782].

    CAS  Google Scholar 

  66. J. Hajdu, P. Fridrich, Anal. Biochem., 1975, 65, 273.

    Article  CAS  Google Scholar 

  67. K. Okuda, I. Urabe, Y. Yamada, H. Okada, J. Ferment. Bioeng., 1991, 71, 100.

    Article  CAS  Google Scholar 

  68. T. J. H. Johnson, in Biocatalysis Design for Stability and Specifity, Eds M. E. Himmel, G. Georgion, ACS Symposium Ser., Am. Chem. Soc. Publ., Washington D.C., 1993, Vol. 516, 283.

  69. N. P. Kuznetsova, L. R. Gudkin, S. V. Kol’tsova, R. N. Mishaeva, Vysokomolekulyar. Soedinen., Ser. A, 1996, 38, 1668 [Polym. Sci., Ser. A (Engl. Transl.), 1996, 38, 1081].

    CAS  Google Scholar 

  70. A. R. Goldfarb, Biochemistry, 1966, 5, 2574.

    Article  CAS  Google Scholar 

  71. D. M. Blow, in The Enzyme, Ed. P. D. Boyer, Acad. Press., New York, 1971, Vol. 3, 185.

  72. D. Hopwood, Histochemie, 1969, 17, 151.

    Article  CAS  Google Scholar 

  73. B. Solomon, N. Lotan, E. Katchalski-Katzir, Biopolymers, 1977, 16, 1837.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Institute of Macromolecular Compounds, Russian Academy of Sciences, 31 B. O. Bol’shoi prosp., 199004, St. Petersburg, Russian Federation

    N. P. Kuznetsova, R. N. Mishaeva, L. R. Gudkin & E. F. Panarin

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  1. N. P. Kuznetsova
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  2. R. N. Mishaeva
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  3. L. R. Gudkin
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  4. E. F. Panarin
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Correspondence to N. P. Kuznetsova.

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Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 0918–0928, April, 2013.

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Kuznetsova, N.P., Mishaeva, R.N., Gudkin, L.R. et al. Reactions of glutaraldehyde with dipolar ions of amino acids and proteins. Russ Chem Bull 62, 918–927 (2013). https://doi.org/10.1007/s11172-013-0122-1

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