Proline Analogs

By: Matthias Junkers, Chemfiles Volume 10 Article 4

Proline is a non-polar, natural amino acid that forms a tertiary amide when incorporated into peptides. Thus, it is the only proteinogenic amino acid that does not act as a hydrogen bond donor in a peptide chain. Proline is known as a classical breaker of both the α-helical and β-sheet secondary structures in proteins and peptides, and it plays a crucial role in protein folding. Synthetic proline derivatives, mimetics and analogs off er further options to tune the biological, pharmaceutical, or physicochemical properties of peptides and proteins.

In recent years proline derivatives and analogs have also found increasing popularity as organocatalysts in asymmetric synthesis.1

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References

  1. (a) Vignola, N.; List, B. J. Am. Chem. Soc. 2003, 125, 450. (b) Dalko, P.I.; Moisan, L.; Angew. Chem. Int. Ed. 2004, 43, 5138.

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