title: Coassembly of amphiphiles with opposite peptide polarities into nanofibers.
abstract: The design, synthesis, and characterization of "reverse" peptide amphiphiles (PAs) with free N-termini is described. Use of an unnatural amino acid modified with a fatty acid tail allows for the synthesis of this new class of PA molecules. The mixing of these molecules with complementary ones containing a free C-terminus results in coassembled structures, as demonstrated by circular dichroism and NOE/NMR spectroscopy. These assemblies show unusual thermal stability when compared to assemblies composed of only one type of PA molecule. This class of reverse PAs has made it possible to create biologically significant assemblies with free N-terminal peptide sequences, which were previously inaccessible, including those derived from phage display methodologies.
authors.affiliation: Department of Chemistry, Institute for BioNanotechnology in Medicine, Northwestern University, Evanston, Illinois 60208, USA.
authors.forename: Heather A
authors.initials: HA
authors.lastname: Behanna
authors.forename: Jack J J M
authors.initials: JJ
authors.lastname: Donners
authors.forename: Alex C
authors.initials: AC
authors.lastname: Gordon
authors.forename: Samuel I
authors.initials: SI
authors.lastname: Stupp
mesh_terms: D000478:Alkylation; D000595:Amino Acid Sequence; D000596:Amino Acids / Q000737:chemistry; D002942:Circular Dichroism; D005449:Fluorenes / Q000737:chemistry; D018698:Glutamic Acid / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D008239:Lysine / Q000737:chemistry; D008969:Molecular Sequence Data; D049329:Nanostructures / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D019308:Palmitic Acid / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D017433:Protein Structure, Secondary; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D000596:Amino Acids; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D010455:Peptides; D019308:Palmitic Acid; D018698:Glutamic Acid; D008239:Lysine