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Solid-phase total synthesis of polymyxin B1.

S K Sharma1, A D Wu, N Chandramouli

  • 1Oncology Department, Novartis Institute of Biomedical Research, Summit, NY 07901-1398, USA. SUSHIL.SHARMA@PHARMA.NOVARTIS.COM

The Journal of Peptide Research : Official Journal of the American Peptide Society
|July 29, 1999
PubMed
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Researchers achieved the total solid-phase synthesis of polymyxin B1, a complex peptide antibiotic. This method offers a viable route for producing this vital compound, demonstrating high yield and purity.

Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Biotechnology

Background:

  • Polymyxin B1 is a critical antibiotic used to treat severe bacterial infections.
  • The complex macrocyclic structure of polymyxin B1 presents significant synthetic challenges.
  • Existing methods for polymyxin B1 production are often inefficient or difficult to scale.

Purpose of the Study:

  • To develop a robust and efficient total solid-phase synthesis of polymyxin B1.
  • To demonstrate the feasibility of synthesizing complex peptide macrocycles using solid-phase techniques.
  • To provide a reliable method for producing high-purity synthetic polymyxin B1.

Main Methods:

  • Utilized solid-phase synthesis methodology.
  • Employed the orthogonal protecting group N-1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl (Dde).

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  • Analyzed the synthetic peptide using Mass Spectrometry (MS) and High-Performance Liquid Chromatography (HPLC).

    • Main Results:

    • Successfully achieved the total solid-phase synthesis of polymyxin B1.
    • Obtained a 20% yield for the synthetic polymyxin B1.
    • Confirmed the identity and purity of the synthetic peptide, matching the naturally occurring antibiotic via MS and HPLC analysis.

    Conclusions:

    • The developed solid-phase synthesis is effective for producing complex peptide macrocycles like polymyxin B1.
    • This method offers a high-yield and high-purity route to synthetic polymyxin B1.
    • The synthetic polymyxin B1 is indistinguishable from the natural antibiotic, validating the synthesis approach.