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A preorganized β-amino acid bearing a guanidinium side chain and its use in cell-penetrating peptides†
Makoto Oba,Takashi Misawa,Masakazu Tanaka,Samuel H. Gellman
Organic & Biomolecular Chemistry Pub Date : 04/14/2015 00:00:00 , DOI:10.1039/C5OB00389J
Abstract

A cyclic β-amino acid (APCGu) bearing a side-chain guanidinium group has been developed. The APCGu residue was incorporated into an α/β-peptide based on the Tat(47–57) fragment, leading to an oligomer with substantial helicity in methanol that enters HeLa cells much more readily than does the corresponding Tat α-peptide.

Graphical abstract: A preorganized β-amino acid bearing a guanidinium side chain and its use in cell-penetrating peptides
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