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Efficient solid-phase-based total synthesis of the bisintercalator TANDEM.

John P Malkinson1, Michael K Anim, Mire Zloh

  • 1Department of Pharmaceutical and Biological Chemistry, School of Pharmacy, University of London, 29-39 Brunswick Square, London WC1N 1AX, UK. john.malkinson@ulsop.ac.uk

The Journal of Organic Chemistry
|September 10, 2005
PubMed
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Researchers developed a novel solid-phase synthesis for TANDEM, a triostin A analogue. This improved method enhances efficiency for creating TANDEM and related compounds for structure-activity relationship studies.

Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Molecular Biology

Background:

  • Triostin A is a natural product with DNA-binding properties.
  • Developing synthetic analogues like TANDEM is crucial for understanding structure-activity relationships.
  • Previous syntheses of TANDEM have limitations in efficiency and yield.

Purpose of the Study:

  • To develop the first solid-phase-based total synthesis of TANDEM.
  • To optimize the synthetic route for higher overall yield and efficiency.
  • To enable further structure-activity relationship studies of TANDEM and triostin A analogues.

Main Methods:

  • Solid-phase synthesis incorporating depsipeptide formation, chromophore introduction, and disulfide bond formation.
  • Comparison of two synthetic strategies: on-resin disulfide formation versus solution-phase disulfide formation after cleavage.

Related Experiment Videos

  • Macrolactamization under mild conditions and high dilution.
  • DNase I footprinting to assess DNA binding affinity.

    • Main Results:

    • Initial solid-phase approach yielded TANDEM with a low cyclization yield (11%).
    • An optimized strategy involving cleavage before disulfide bond formation resulted in a 18% overall yield.
    • The optimized synthesis provided pure TANDEM efficiently.
    • DNase I footprinting confirmed TANDEM's ability to bind to 5 ahydro-TpA sequences on DNA.

    Conclusions:

    • A novel and efficient solid-phase synthesis of TANDEM has been established.
    • The optimized synthetic route facilitates the production of TANDEM for further biological evaluation.
    • This work paves the way for systematic structure-activity relationship studies of TANDEM and triostin A analogues.