Molecular Engineering of the Peptoid Nanosheet Hydrophobic Core
| Autor: | Jessica K. Su, Laudann Taravati, Stan Yoo, Ronald N. Zuckermann, Caroline Proulx, Eric Michael Nehls, Rita L. Garcia, Ellen J. Robertson, Michael D. Connolly |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
Nanostructure Peptoid nanosheet Sequence (biology) Nanotechnology Peptoid 02 engineering and technology Surfaces and Interfaces Polymer 010402 general chemistry 021001 nanoscience & nanotechnology Condensed Matter Physics 01 natural sciences Combinatorial chemistry 0104 chemical sciences Molecular engineering chemistry.chemical_compound Monomer chemistry Electrochemistry General Materials Science 0210 nano-technology Spectroscopy Nanosheet |
| Zdroj: | Langmuir : the ACS journal of surfaces and colloids. 32(45) |
| ISSN: | 1520-5827 |
| Popis: | The relationship between the structure of sequence-defined peptoid polymers and their ability to assemble into well-defined nanostructures is important to the creation of new bioinspired platforms with sophisticated functionality. Here, the hydrophobic N-(2-phenylethyl)glycine (Npe) monomers of the standard nanosheet-forming peptoid sequence were modified in an effort to (1) produce nanosheets from relatively short peptoids, (2) inhibit the aggregation of peptoids in bulk solution, (3) increase nanosheet stability by promoting packing interactions within the hydrophobic core, and (4) produce nanosheets with a nonaromatic hydrophobic core. Fluorescence and optical microscopy of individual nanosheets reveal that certain modifications to the hydrophobic core were well tolerated, whereas others resulted in instability or aggregation or prevented assembly. Importantly, we demonstrate that substitution at the meta and para positions of the Npe aromatic ring are well tolerated, enabling significant opportunities to tune the functional properties of peptoid nanosheets. We also found that N-aryl glycine monomers inhibit nanosheet formation, whereas branched aliphatic monomers have the ability to form nanosheets. An analysis of the crystal structures of several N,N'-disubstituted diketopiperazines (DKPs), a simple model system, revealed that the preferred solid-state packing arrangement of the hydrophobic groups can directly inform the assembly of stable peptoid nanosheets. |
| Databáze: | OpenAIRE |
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