Skip to main content
SpringerLink
Log in

A Convenient Microwave-Enhanced Solid-Phase Synthesis of Difficult Peptide Sequences: Case Study of Gramicidin A and CSF114(Glc)

  • Bruce Merrifield Commemorative Issue
  • Published:
International Journal of Peptide Research and Therapeutics Aims and scope Submit manuscript

 

Taking into account that microwave technology applied to SPPS is proposed as a valid support to the enhancement of efficiency of coupling reactions in short times, we compared the efficacy of a new automatic monomode microwave instrument versus a traditional automatic peptide synthesizer in the synthesis of different difficult peptide sequences. We verified that microwave-assisted solid phase synthesis is convenient, in terms of yield, purity, and time consumed to prepare two peptides which were previously shown to be difficult to obtain by conventional strategy, i.e., the antibiotic Gramicidin A and a glycopeptide.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.
Fig. 6.

Similar content being viewed by others

References

  • Albericio F. (2004) Curr. Opin. Chem. Biol., 8, 211–221

    Article  PubMed  CAS  Google Scholar 

  • Borgia, J. A., Fields, G. B. (2000), Trends Biotechnol. 18, 243–251

    Article  PubMed  CAS  Google Scholar 

  • Fields G. B., Fields C. G., Petefish J., Van Wart H. E., Cross T. A. (1988), Proc. Natl. Acad. Sci. USA. 85, 1384–1388

    Article  PubMed  CAS  Google Scholar 

  • Gedye R. Smith F., Westaway K., Ali H., Baldisera L., Laberge L., Rousell J. (1986), Tetrahedron Lett. 27, 279–282

    Article  CAS  Google Scholar 

  • Giguere R. J., Bray T. L., Duncan S. M., Majetich G. (1986), Tetrahedron Lett., 27, 4945–4948

    Article  CAS  Google Scholar 

  • Han S.-Y., Kim Y.-A. (2004), Tetrahedron 60 2447–2467

    Article  CAS  Google Scholar 

  • Hancock R. E. W., Chapple D. S. (1999), Antimicrob. Agents Chemother., 43, 1317–1323

    PubMed  CAS  Google Scholar 

  • Hayes, B. L.: 2002, in: Microwave Synthesis: Chemistry at the Speed of Light, CEM Publishing, Matthews, NC

  • Kappe C. O. (2004), Angew. Chem. Int. Ed., 43, 6250–6284

    Article  CAS  Google Scholar 

  • Lolli F., Mazzanti B., Pazzagli M., Peroni E., Alcaro M. C., Sabatino G., Lanzillo R., Brescia Morra V., Santoro L., Gasperini C., Galgani S., D’Elios M. M., Zipoli V., Sotgiu S., Pugliatti M., Rovero P., Chelli M., Papini A. M. (2005a), J. Neuroimmunol. 167, 131–137

    Article  CAS  Google Scholar 

  • Lolli F., Mulinacci B., Carotenuto A., Bonetti B., Sabatino G., Mazzanti B., D’Ursi A. M., Novellino E., Pazzagli M., Lovato L., Alcaro M. C., Peroni E., Pozo-Carrero M. C., Nuti F., Battistini L., Borsellino G., Chelli M., Rovero P., Papini A. M. (2005b), Proc. Natl. Acad. Sci. USA. 102, 10273–10278

    Article  CAS  Google Scholar 

  • Merrifield R. B. (1963), J. Am. Chem. Soc. 85, 2149–2154

    Article  CAS  Google Scholar 

  • Papini, A. M., Chelli, M., Rovero, P. and Lolli, F. inventors: 2003, Preparation of glycopeptides for use in the diagnosis or therapeutic treatment of multiple sclerosis. Italy. International Patent Application (2003), number WO 03/000733 A2

  • Souza, M. P., Tavares, M. F. M. and Miranda, M. T. M.: 2004, Tetrahedron 60, 4671–4681

    Article  CAS  Google Scholar 

  • Yu H. M., Chen S. T., Wang K. T. (1992), J. Org. Chem., 57, 4781–4784

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Laboratory of Peptide & Protein Chemistry & Biology, Polo Scientifico e Tecnologico, Università di Firenze, 50019, Sesto Fiorentino, FI, Italy

    Fabio Rizzolo, Giuseppina Sabatino, Mario Chelli, Paolo Rovero & Anna Maria Papini

  2. Dipartimento di Chimica Organica “Ugo Schiff” and CNR-ICCOM, Polo Scientifico, Università di Firenze, Via della Lastruccia, 13, 50019, Sesto Fiorentino, FI, Italy

    Fabio Rizzolo, Giuseppina Sabatino, Mario Chelli & Anna Maria Papini

  3. Dipartimento di Scienze Farmaceutiche, Università di Firenze, 50019, Sesto Fiorentino, FI, Italy

    Paolo Rovero

Authors
  1. Fabio Rizzolo
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Giuseppina Sabatino
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mario Chelli
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Paolo Rovero
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Anna Maria Papini
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Anna Maria Papini.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Rizzolo, F., Sabatino, G., Chelli, M. et al. A Convenient Microwave-Enhanced Solid-Phase Synthesis of Difficult Peptide Sequences: Case Study of Gramicidin A and CSF114(Glc). Int J Pept Res Ther 13, 203–208 (2007). https://doi.org/10.1007/s10989-006-9066-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10989-006-9066-8

Keywords

Search

Navigation