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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
A versatile annulation protocol toward novel constrained phosphinic peptidomimetics
Magdalini Nasopoulou1, Dimitris Georgiadis, Magdalini Matziari
1Department of Chemistry, Laboratory of Organic Chemistry, University of Athens, Panepistimiopolis Zografou 15771, Athens, Greece.
The Journal of Organic Chemistry
|August 25, 2007
Summary
A new reaction creates diverse phosphinic acid scaffolds for peptidomimetics. This method yields Fmoc-protected constrained aminophosphinic acids, useful for solid-phase peptide synthesis and further derivatization.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Synthetic Chemistry
Background:
- Phosphinic acids are crucial in medicinal chemistry.
- Developing efficient synthetic routes to novel phosphinic acid derivatives is essential for drug discovery.
- Constrained scaffolds offer unique pharmacological properties.
Purpose of the Study:
- To report a novel 3-center 2-component annulation reaction.
- To synthesize diverse phosphinic acid scaffolds with controlled structural features.
- To develop building blocks for peptidomimetic synthesis.
Main Methods:
- Reaction of alpha,omega-carbamoylaldehydes with monoalkylated phosphinic acids.
- One-step synthesis of phosphinic scaffolds.
- Fmoc protection for solid-phase peptide synthesis compatibility.
Main Results:
- High yields of diverse phosphinic scaffolds achieved.
- Structural variability includes rigidity, substituents, and heteroatom incorporation.
- Synthesis of Fmoc-protected constrained aminophosphinic acids demonstrated.
Conclusions:
- The novel annulation reaction provides efficient access to functionalized phosphinic scaffolds.
- The methodology enables the synthesis of pseudodipeptide building blocks for solid-phase peptide synthesis.
- Orthogonally protected scaffolds allow for extensive derivatization of phosphinic peptidomimetics.
