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Issue 25, 2018
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Polypeptide gels incorporating the exotic functional aromatic amino acid 4-amino-l-phenylalanine

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Abstract

High-molecular-weight polypeptides with functional aromatic side chains, poly(4-amino-L-phenylalanine), 4APhe, were prepared by the metal-initiated polymerization of the Nα-carboxyanhydride of the corresponding amino acid, which is a microbial derivative of phenylalanine. The polypeptide P4APhe has good water solubility as opposed to those of the conventional aromatic poly(amino acid)s such as poly(L-phenylalanine) or poly(L-tyrosine). On the other hand, P4APhe shows an in situ gelation ability upon the swelling of dried samples in solvents, due to the formation of crystalline β-sheet domains that work as cross-linking junctions. Moreover, the cationic copolymers of 4APhe with L-lysine showed a pH-responsive gelling behavior resulting from changes in the amphipathic balance of crystalline β-strands, α-helical structures, and hydrophilic random coils. Notably, small amounts of 4APhe units in copolypeptides with L-lysine were found to enhance adoption α-helical conformations.

Graphical abstract: Polypeptide gels incorporating the exotic functional aromatic amino acid 4-amino-l-phenylalanine

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Supplementary files

Article information


Submitted
17 Mar 2018
Accepted
27 Apr 2018
First published
30 Apr 2018

Polym. Chem., 2018,9, 3466-3472
Article type
Paper
Author version available

Polypeptide gels incorporating the exotic functional aromatic amino acid 4-amino-L-phenylalanine

T. Kaneko, M. A. Ali, I. Captain, P. Perlin and T. J. Deming, Polym. Chem., 2018, 9, 3466 DOI: 10.1039/C8PY00427G

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