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  • Title: Cell-penetrating cis-gamma-amino-l-proline-derived peptides.
    Author: Farrera-Sinfreu J, Giralt E, Castel S, Albericio F, Royo M.
    Journal: J Am Chem Soc; 2005 Jul 06; 127(26):9459-68. PubMed ID: 15984873.
    Abstract:
    The synthesis of cis-gamma-amino-l-proline oligomers functionalized at the proline alpha-amine with several groups that mimic the side chains of natural amino acids, including alanine, leucine, and phenylalanine, is herein described. These gamma-peptides enter into different cell lines (COS-1 and HeLa) via an endocytic mechanism. The ability of these compounds to be taken up into cells was studied at 37 degrees C and 4 degrees C by plate fluorimetry, flow cytometry, and confocal microscopy. In addition to their capacity for cellular uptake, these unnatural short length oligomers offer advantages over the well-known penetrating TAT peptide, such as being less toxic than TAT and protease resistance.
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