Unnatural Amino Acid: 4-Aminopyrazolonyl Amino Acid Comprising Tri-Peptides Forms Organogel With Co-Solvent (EtOAc:Hexane)

Abstract

Ampyrone is an amino-functionalized heterocyclic pyrazolone derivative that possesses therapeutic values such as analgesic, anti-inflammatory, and antipyretics. The chemical structure of ampyrone exhibits excellent hydrogen bonding sites and is considered as the potential scaffold of supramolecular self-assembly. Recently, this molecule has been derived into unnatural amino acids such as aminopyrazolone amino acid and its peptides. This report describes that one of its amino acids, O-alkylated ampyrone, containing hybrid (α/β) peptides forms organogel after sonication at 50–55°C with 0.7–0.9% (w/v) in ethyl acetate: hexane (1:3). The formation/morphology of such organogels is studied by nuclear magnetic resonance Fourier-transform infrared (FT-IR), circular dichroism (CD), scanning electron microscope (SEM), transmission electron microscopy (TEM), powder X-ray diffraction (Powder-XRD), and thermogravimetric analysis (TGA). Energy-minimized conformation of APA-peptides reveals the possibility of intermolecular hydrogen bonding. Hence, APA-peptides are promising peptidomimetics for the organogel-peptides.

Sonication-Induced Boladipeptide-Based Metallogel as an Efficient Electrocatalyst for the Oxygen Evolution Reaction

“…On the other hand, the peaks at ∼2θ = 18.54 and 18.7° reveal the interstrand and intersheet distance between two β-sheets (Figure b) . Additionally, the peaks at ∼2θ = 20.67° (with a d -spacing of 4.29 Å) and ∼2θ = 20.37° (with a d -spacing of 4.35 Å) for PBFY and Ni-PBFY-3, respectively, indicate the presence of hydrogen bonding between β-strands . The mechanical properties and viscoelastic behavior of the self-assembled boladipeptide were investigated by using rheological analysis.…”

“…30 Additionally, the peaks at ∼2θ = 20.67°(with a d-spacing of 4.29 Å) and ∼2θ = 20.37°(with a d-spacing of 4.35 Å) for PBFY and Ni-PBFY-3, respectively, indicate the presence of hydrogen bonding between β-strands. 31 The mechanical properties and viscoelastic behavior of the selfassembled boladipeptide were investigated by using rheological analysis. A frequency of 10 rad s −1 was used for the amplitude sweep assessment, and the strain was varied from 0.1 to 100%.…”

Morphological Evaluation of Supramolecular Soft Materials Obtained through Co-Assembly Processes

“…The presence of a peak at 4.2 Å is attributed to π-π stacking. The reflection peaks at 4.6 Å and 5.1 Å which appear in the XRD diffractogram of the M2 gelator correspond to hydrogen bonding between β-strands [29]. The XRD diffractograms of M3 and M4 show similar packing with slight differences.…”

“…The XRD diffractogram of the M1 self-assembled system shows a broad zone of different peak intensities with their d-spacing values between 2-6 Å associated with an amorphous phase [28]. Furthermore, the peaks of d-spacing at 4.9 Å and 10.54 Å are attributed to the inter-sheet distance or to antiparallel β-strands spacing [29]. The presence of a peak at 4.2 Å is attributed to π-π stacking.…”