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Related Experiment Videos

A nonacid degradable linker for solid-phase synthesis.

Aina Colombo1, Natalia De la Figuera, Joan Carles Fernàndez

  • 1Almirall-Barcelona Science Park Unit, Josep Samitier 1-5, E-08028 Barcelona, Spain.

Organic Letters
|September 18, 2007
PubMed
Summary
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Two novel nonacid degradable linkers offer an alternative to the Wang linker in solid-phase synthesis. Linker 2 demonstrates superior performance, improving yields and product purity while avoiding side reactions common with Wang resin.

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Polymer Chemistry

Background:

  • Solid-phase synthesis relies on robust linkers for attaching building blocks to resin supports.
  • The Wang linker is widely used but can be susceptible to cleavage during final acidic treatments, leading to side reactions.
  • Developing alternative linkers is crucial for improving efficiency and purity in solid-phase synthesis.

Purpose of the Study:

  • To synthesize and evaluate two new nonacid degradable linkers as alternatives to the conventional Wang linker.
  • To compare the performance of the new linkers against each other and the Wang linker in solid-phase synthesis.
  • To assess the impact of linker choice on anchoring yields, cleavage efficiency, and final product purity.

Main Methods:

  • Synthesis of two novel nonacid degradable linker molecules.

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  • Attachment of the first building block to resins functionalized with the new linkers and the Wang linker.
  • Cleavage of the synthesized products from the resins under specific conditions.
  • Analysis of anchoring yields, cleavage efficiency, and purity of the final products using analytical techniques.

    • Main Results:

    • Both synthesized linkers were successfully prepared and utilized in solid-phase synthesis.
    • Resin derived from linker 2 exhibited higher yields in both the initial anchoring of the first building block and the final cleavage step compared to linker 1.
    • The final products obtained using linker 2 showed higher purity than those synthesized with linker 1.
    • Linker 2 effectively avoided undesired side reactions, such as premature cleavage, that can occur with the Wang linker during final acid treatment.

    Conclusions:

    • The newly developed nonacid degradable linkers provide viable alternatives to the Wang linker for solid-phase synthesis.
    • Linker 2 is a superior option, offering enhanced yields and improved purity of the final products.
    • The use of linker 2 mitigates side reactions associated with the Wang linker, leading to more efficient and reliable synthetic outcomes.