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The solid phase coupling of peptide segments catalyzed by the subtilisin-sodium dodecyl sulfate complex

Abstract

The subtilisin-sodium dodecyl sulfate complex was shown to catalyze the coupling of peptide segments on a solid phase in organic medium. By a two-stage enzymic condensation of peptide fragments on aminosilochrom (A) containing Met-Ala-Gly as a spacer, Dnp(or Boc)-Ala-Ala-Leu-Ala-Ala-Glu(OMe)-Met-Ala-Gly-A and Z-Ala-Ala-Glu(OMe)-Ala-Ala-Leu-Met-Ala-Gly-A were obtained. It was shown that the condensation products can be split off from the support using Met residue cleavage by BrCN.

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Abbreviations

Hse:

homoseryl residue

pNA:

p-nitroanilide

SDS:

sodium dodecyl sulfate

SPS:

solid phase peptide synthesis

References

  1. Könnecke, A., Dettlaff, S., and Jakubke, H.-D.,Monatsh. Chem., 1982, vol. 113, pp. 331–337.

    Article  Google Scholar 

  2. Slomczynska, U., Albericio, F., Cardenas, F., and Giralt, E.,Biomed. Biochim. Acta, 1991, vol. 50, pp. 67–73.

    Google Scholar 

  3. Meyer, J.D., Kendric, B.S., Matsuura, J.E., Ruth, J.A., Bryan, P.N., and Manning, M.,Int. J. Peptide Protein Res., 1996, vol. 47, pp. 177–181.

    CAS  Article  Google Scholar 

  4. Kendric, B.S., Meyer, J.D., Matsuura, J.E., Carpenter, J.F., and Manning, M.,Arch. Biochem. Biophys., 1997, vol. 347, pp. 113–118.

    Article  Google Scholar 

  5. Wangikar, P.P., Michels, P.C., Clark, D.S., and Dordick, J.S.,J. Am. Chem. Soc., 1997, vol. 119, pp. 70–76.

    Article  CAS  Google Scholar 

  6. Moree, W.J., Sears, P., Kawashiro, K., Witte, K., and Wong, C.-H.,J. Am. Chem. Soc., 1997, vol. 119, pp. 3942–3947.

    Article  CAS  Google Scholar 

  7. Potetinova, J.V., Voyushina, T.L., and Stepanov, V.M.,Bioorg. Med. Chem. Lett., 1997, vol. 7, pp. 705–710.

    Article  CAS  Google Scholar 

  8. Getun, I.V., Filippova, I.Yu., Lysogorskaya, E.N., Oksenoit, E.S., Anisimova, V.V., Kolobanova, S.V., Bacheva, A.V., and Stepanov, V.M.,Bioorg. Med. Chem. Lett., 1997, vol. 7, pp. 2691–2696.

    Article  CAS  Google Scholar 

  9. Stewart, J.M. and Young, J.D.,Solid Phase Peptide Synthesis, San Francisco: W.H. Freeman & Co., 1969. Translated under the titleTverdofaznyi sintez peptidov, Moscow: Mir, 1971.

    Google Scholar 

  10. Renil, M., Ferreras, M., Delaisse, J.M., Foged, N.T., and Meldal, M.,J. Peptide Sci., 1998, vol. 4, pp. 195–210.

    Article  CAS  Google Scholar 

  11. Meldal, M., Svendsen, I., Juliano, L., Nery, E.D., and Scharfstein, J.J.,J. Peptide Sci., 1998, vol. 4, pp. 83–91.

    Article  CAS  Google Scholar 

  12. Spetzler, J.C., Westphal, V., Winther, J.R., and Meldal, M.,J. Peptide Sci., 1998, vol. 4, pp. 128–137.

    Article  CAS  Google Scholar 

  13. Stepanov, V.M., Rudenskaya, G.N., Gaida, A.V., and Osterman, A.L.,J. Biochem. Biophys. Methods, 1981, vol. 5, pp. 177–186.

    PubMed  Article  CAS  Google Scholar 

  14. Lyublinskaya, L.A., Yusupova, M.P., Vaganova, T.I., Ivanova, N.M., and Stepanov, V.M.,Bioorg. Khim., 1984, vol. 10, pp. 1490–1495.

    CAS  Google Scholar 

  15. Darbre, A.,Practical Protein Chemistry: A Handbook, Chichester: John Wiley & Sons Ltd., 1986. Translated under the titlePrakticheskaya khimiya belka, Moscow: Mir, 1989.

    Google Scholar 

  16. Gershkovich, A.A. and Kibirev, V.K.,Khimicheskii sintez peptidov (Chemical Synthesis of Peptides), Kiev: Naukova Dumka, 1992.

    Google Scholar 

  17. Gololobov, M.Yu., Morozova, I.P., and Stepanov, V.M.,Biokhimiya (Moscow), 1991, vol. 56, pp. 33–40.

    CAS  Google Scholar 

  18. Lyublinskaya, L.A., Khaidu, I., Balandina, G.N., Filippova, I.Yu., Markaryan, A.N., Lysogorskaya, E.N., Oksenoit, E.S., and Stepanov, V.M.,Bioorg. Khim., 1987, vol. 13, pp. 748–753.

    CAS  Google Scholar 

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Correspondence to I. Yu. Filippova.

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Deceased.

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Kolobanova, S.V., Filippova, I.Y., Lysogorskaya, E.N. et al. The solid phase coupling of peptide segments catalyzed by the subtilisin-sodium dodecyl sulfate complex. Russ J Bioorg Chem 26, 369–374 (2000). https://doi.org/10.1007/BF02758663

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  • DOI: https://doi.org/10.1007/BF02758663

Key words

  • enzymic peptide synthesis
  • solid support
  • SDS-subtilisin