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Incorporation of a Non‐Natural Arginine Analogue into a Cyclic Peptide Leads to Formation of Positively Charged Nanofibers Capable of Gene Transfection
Author(s) -
Li Mao,
Ehlers Martin,
Schlesiger Stefanie,
Zellermann Elio,
Knauer Shirley K.,
Schmuck Carsten
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201508714
Subject(s) - peptide , transfection , cationic polymerization , moiety , nanofiber , surface modification , cyclic peptide , biophysics , dna , chemistry , combinatorial chemistry , arginine , materials science , nanotechnology , stereochemistry , biochemistry , amino acid , gene , polymer chemistry , biology
Abstract Functionalization of the tetracationic cyclic peptide (Ka) 4 with a single guanidiniocarbonyl pyrrole (GCP) moiety, a weakly basic but highly efficient arginine analogue, completely alters the self‐assembly properties of the peptide. In contrast to the nonfunctionalized peptide 2 , which does not self‐assemble, GCP‐containing peptide 1 forms cationic nanofibers of micrometer length. These aggregates are efficient gene transfection vectors. DNA binds to their cationic surface and is efficiently delivered into cells.