Abstract
Peptide segments corresponding to antibacterial esculentin-1 (1–15), (33–44), (9–27), and their modified forms were synthesized on 1,4-butanediol dimethacrylate cross-linked polystyrene (PS-BDODMA) support. Hydroxymethyl and aminomethyl 2% PS-BDODMA supports were used for the synthesis. The HMPB linker was appended to the aminomethyl resin using HBTU in presence of HOBt and the first amino acid was incorporated using MSNT. The conventional Fmoc synthetic protocol was used for the synthesis of peptides. The peptides were cleaved from the support using TFA. The peptides were purified by HPLC, and characterized by amino acid analysis and MALDI TOF MS. The secondary structures of the peptides were revealed by CD measurements. The synthesis of these peptides illustrates the utility of the new support for the synthesis of long-chain bioactive peptides. The synthetic peptides were tested for antimicrobial activity against Escherichia coli Mos blue, E. coli 2, Bacillus brevis, B. megaterium, Pseudomonas HTL, and Vibrio mimicus. The antibacterial activity of the peptides was explained on the basis of the helicity and charged nature of the sequences.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
Arshady, R., Atherton, E., Clive, D. L. J., and Sheppard, R. C. (1981). J.Chem.Soc.Perkin Trans. 1, 529–537.
Barany, G. and Merrifield, R. B. (1979). In The Peptides (Gross, E., and Meinhofer, J., eds.), Academic Press, New York, Vol. 2, pp. 1–289.
Bevins, C. L. and Zasloff, M. (1990). Annu.Rev.Biochem. 59, 395–414.
Daly, J. W. (1995). Proc.Natl.Acad.Sci.USA 92, 9–13.
Engelbresten, D. R. and Harding, D. R. K. (1994). Int.J.Peptide Protein Res. 43, 546–554.
Erspamer, V. (1994). In Amphibian Biology (Heatwole, H., ed.), Surrey Beatty & Sons, Chipping Northon, England, Vol. 1, pp. 178–350.
Erspamer, V. and Melchiorri, P. (1980). Trends Pharmacol.Sci. 1, 391–395.
Florsheimer, A. and Riniker, B. (1991). In Peptides 1990, Proceedings 21st European Peptide Symposium (Giralt, E., and Andrew, D., eds.), ESCOM, Leiden, p. 131.
Hellerman, H., Lucas, H. W., Maul, J., Pillai, V. N. R., and Mutter, M. (1983). Makromol.Chem. 184, 2603–2617.
Hodge, D. C. and Sherrington, D. C. (1988). Polymer Supported Reactions in Organic Chemistry, Wiley, Chichester, England.
Houghten, R. A., Pinilla, C., Blondelle, S. E., Appel, J. R., Dooley, C. T., and Cuervo, J. H. (1991). Nature 354, 84–86.
Kaiser, E., Colescott, R. L., Bossinger, C. D., and Cook, P. I. (1970). Anal.Biochem. 34, 595–598.
Kempe, M. and Barany, G. (1996). J.Am.Chem.Soc. 118, 7083–7093.
Lam, K. S., Salmon, S. E., Hersh, E. M., Hurby, V. J., Kazmicrski, W. M., and Knapp, R. J. (1991). Nature 354, 82–84.
Meldal, M. (1992). Tetrahedron Lett. 33, 3077–3080.
Meldal, M. (1997). In Solid-Phase Peptide Synthesis (Fields, G., ed.), Academic Press, New York, pp. 83–104.
Merrifield, R. B. (1963). J.Am.Chem.Soc. 85, 2149–2153.
Redemann, J., Grotli, M., Meldal, M., and Bock, K. (1999). J.Am.Chem.Soc. 121, 5459–5466.
Renil, M. and Meldal, M. (1996). Tetrahedron Lett. 37, 6185–6188.
Renil, M., Nagaraj, R., and Pillai, V. N. R. (1994). Tetrahedron 50, 6681–6688.
Roice, M., Kumar, K. S., and Pillai, V. N. R. (1999). Macromolecules 32, 8807–8815.
Roice, M., Kumar, K. S., and Pillai, V. N. R. (2000). Tetrahedron 56, 3725–3734.
Simmaco, M., Mignogna, G., Barra, D., and Bossa, F. (1993). FEBS Lett. 324, 159–161.
Simmaco, M., Mignogna, G., Barra, D., and Bossa, F. J. (1994). Biol.Chem. 1994, 11956–11961.
Stewart, J. M. and Young, J. D. (1984). Solid Phase Peptide Synthesis, Pierce Chemical Co., Rockford, Illinois, Vol. 2, p-54.
Varkey, J. T. and Pillai, V. N. R. (1998). J.Peptide Res. 51, 49–54.
Zalipsky, S., Chang, J. L., Albericio, F., and Barany, G. (1994). React.Polym. 22, 243–258.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Roice, M., Suma, G., Kumar, K.S. et al. Synthesis of Esculentin-1 Antibacterial Peptide Fragments on 1,4-Butanediol Dimethacrylate Cross-Linked Polystyrene Support. J Protein Chem 20, 25–32 (2001). https://doi.org/10.1023/A:1011048919748
Published:
Issue Date:
DOI: https://doi.org/10.1023/A:1011048919748