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Microwave assisted synthesis of Py-Im polyamides
James W Puckett1, Joshua T Green, Peter B Dervan
1Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
Organic Letters
|May 15, 2012
Summary
Microwave synthesis rapidly produced high-purity Py-Im polyamides. A synthesized polyamide targeting response elements showed no amino acid racemization, confirming method reliability for complex molecule synthesis.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Molecular Biology
Background:
- Polyamides are versatile molecules with applications in various scientific fields.
- Developing efficient and reliable methods for polyamide synthesis is crucial.
- Protecting group strategies are essential for controlled synthesis of complex molecules.
Purpose of the Study:
- To develop a rapid microwave-assisted synthesis for Py-Im polyamides.
- To synthesize a specific polyamide targeting Androgen and Glucocorticoid Response Elements.
- To confirm the stereochemical integrity of amino acids during synthesis.
Main Methods:
- Microwave synthesis utilizing Boc-protection chemistry on Kaiser oxime resin.
- Solid-phase synthesis of a 20-step linear polyamide.
- High-Performance Liquid Chromatography (HPLC) for purification.
- Mosher amide derivatization for stereochemical analysis.
Main Results:
- Py-Im polyamides were synthesized in high yields and purity.
- A representative polyamide targeting response elements was obtained in 56% yield.
- Mosher amide derivatization confirmed no racemization of chiral α-amino acids.
Conclusions:
- Microwave synthesis offers a rapid and efficient route to Py-Im polyamides.
- The synthetic strategy preserves the stereochemical integrity of chiral amino acids.
- This method is suitable for constructing complex polyamides for biological applications.
