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Stapled Peptides—A Useful Improvement for Peptide-Based Drugs

Department of Chemistry, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy
Author to whom correspondence should be addressed.
Molecules 2019, 24(20), 3654;
Received: 30 July 2019 / Revised: 24 September 2019 / Accepted: 1 October 2019 / Published: 10 October 2019
(This article belongs to the Special Issue Nucleosides: Synthesis and Antiviral Activity)
Peptide-based drugs, despite being relegated as niche pharmaceuticals for years, are now capturing more and more attention from the scientific community. The main problem for these kinds of pharmacological compounds was the low degree of cellular uptake, which relegates the application of peptide-drugs to extracellular targets. In recent years, many new techniques have been developed in order to bypass the intrinsic problem of this kind of pharmaceuticals. One of these features is the use of stapled peptides. Stapled peptides consist of peptide chains that bring an external brace that force the peptide structure into an α -helical one. The cross-link is obtained by the linkage of the side chains of opportune-modified amino acids posed at the right distance inside the peptide chain. In this account, we report the main stapling methodologies currently employed or under development and the synthetic pathways involved in the amino acid modifications. Moreover, we report the results of two comparative studies upon different kinds of stapled-peptides, evaluating the properties given from each typology of staple to the target peptide and discussing the best choices for the use of this feature in peptide-drug synthesis. View Full-Text
Keywords: stapled peptide; structurally constrained peptide; cellular uptake; helicity; peptide drugs stapled peptide; structurally constrained peptide; cellular uptake; helicity; peptide drugs
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MDPI and ACS Style

Moiola, M.; Memeo, M.G.; Quadrelli, P. Stapled Peptides—A Useful Improvement for Peptide-Based Drugs. Molecules 2019, 24, 3654.

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