Journal
BIOMACROMOLECULES
Volume 15, Issue 4, Pages 1491-1497Publisher
AMER CHEMICAL SOC
DOI: 10.1021/bm5001026
Keywords
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Funding
- NSF [CHE 11-53122]
- NIH [1DP2OD007246]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1153122] Funding Source: National Science Foundation
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Polypeptides bearing quaternary phosphonium side chains were synthesized via controlled ring-opening polymerization of chlorine-functionalized amino acid N-carboxyanhydride monomers followed by one-step nucleophilic substitution reaction with triethylphosphine. The conformation of the resulting polypeptides can be controlled by modulating the side-chain length and alpha-carbon stereochemistry. The phosphonium-based poly(L-glutamate) derivatives with 11 sigma-bond backbone-to-charge distance adopt stable alpha-helical conformation against pH and ionic strength changes. These helical, quaternary phosphonium-bearing polypeptides exhibit higher cell-penetrating capability than their racemic and random-coiled analogues. They enter cells mainly via an energy-independent, nonendocytic cell membrane transduction mechanism and exhibit low cytotoxicity, substantiating their potential use as a safe and effective cell-penetrating agent.
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