Self-assembling α,γ-cyclic peptides that generate cavities with tunable properties.

Self-assembling α,γ-cyclic peptides that generate cavities with tunable properties† †Electronic supplementary information (ESI) available: Synthetic experimental details, DFT calculation details, additional figures (relevant NMR data) and schemes (synthetic schemes for peptide and amino acid preparation). CCDC 1400134. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc03187g Click here for additional data file. Click here for additional data file.

Self-assembling properties of all γ-cyclic peptides containing sugar amino acid residues.

In this study, a novel dimer-forming cyclic peptide composed exclusively by cyclic γ-amino acids with a saccharide-like outer surface is described. The antiparallel β-sheet type hydrogen bonding interactions responsible for the large association constant in non-polar solvents constitute a suitable model for a novel class of self-assembling peptide nanotubes.

Bioinspired self-assembled peptide nanofibers with thermostable multivalent α-helices.

The stabilization of peptide's active conformation is a critical determinant of its target binding efficiency. Here we present a structure-based self-assembly strategy for the design of nanostructures with multiple and thermostable α-helices using bioinspired peptide amphiphiles. The design principle was inspired by the oligomerization of the human immunodeficiency virus type-1 (HIV-1) Rev prot...

Self-Assembling Cyclic d,l-α-Peptides as Modulators of Plasma HDL Function. A Supramolecular Approach toward Antiatherosclerotic Agents

There is great interest in developing new modes of therapy for atherosclerosis to treat coronary heart disease and stroke, particularly ones that involve modulation of high-density lipoproteins (HDLs). Here, we describe a new supramolecular chemotype for altering HDL morphology and function. Guided by rational design and SAR-driven peptide sequence enumerations, we have synthesized and determin...

Synthesis and conformational analysis of macrocyclic peptides consisting of both α-helix and polyproline helix segments.

Macrocycles are interesting molecules because their topological features and constrained properties significantly affect their chemical, physical, biological, and self-assembling properties. In this report, we synthesized unique macrocyclic peptides composed of both an α-helix and a polyproline segment and analyzed their conformational properties. We found that the molecular stiffness of the ro...