Annada Rajbhandary, W. Brennessel, Bradley L. Nilsson
Jan 23, 2018
Citations
3
Influential Citations
19
Citations
Journal
Crystal Growth & Design
Abstract
Fluorenylmethoxycarbonyl-protected phenylalanine (Fmoc-Phe) derivatives are a privileged class of low molecular weight amino acid hydrogelators that undergo spontaneous self-assembly in water to form one-dimensional (1D) fibril networks. Structural studies indicate that these fibrils feature unidirectional hydrogen bonding and parallel π–π interactions (Fmoc–Fmoc and side chain benzyl–benzyl), which stabilize the 1D fibrils. However, the relative contribution of hydrogen bonding vs π–π interactions in these assemblies is not understood. Herein, we compare the self-assembly of Fmoc-Phe amino acids with corresponding Fmoc-protected peptoid derivatives. The N-benzyl glycine-derived peptoid analogues exhibit altered hydrogen bonding ability and benzyl side chain presentation geometry relative to the parent Fmoc-Phe molecules. We found that Fmoc-peptoid analogues preferentially assemble into two-dimensional (2D) nano- and microsheets that ultimately adopt crystalline states, whereas the Fmoc-Phe amino acids as...