Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Solid-Phase Synthesis of Gly-Ψ[CH(CF₃)NH]-Peptides.

ABSTRACT: The solid-phase synthesis of Gly-Ψ[CH(CF₃)NH]-peptides is presented. In order to achieve this goal, the synthesis of Gly-Ψ[CH(CF₃)NH]-dipeptides having the C-terminus unprotected, the N-terminus protected as Fmoc- or Teoc-, and possibly side chain functionalities protected with acid-labile protecting groups has been developed. A selected small library of six peptidomimetics, encompassing analogues of biological relevant peptides, have been obtained in high purity.

SUBMITTER: Sgorbati C

PROVIDER: S-EPMC8279481 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Solid-Phase Synthesis of Gly-Ψ[CH(CF3)NH]-Peptides.

Sgorbati Clara C Lo Presti Eliana E Bergamaschi Greta G Sani Monica M Volonterio Alessandro A

The Journal of organic chemistry 20210603 13

The solid-phase synthesis of Gly-Ψ[CH(CF3)NH]-peptides is presented. In order to achieve this goal, the synthesis of Gly-Ψ[CH(CF3)NH]-dipeptides having the C-terminus unprotected, the N-terminus protected as Fmoc- or Teoc-, and possibly side chain functionalities protected with acid-labile protecting groups has been developed. A selected small library of six peptidomimetics, encompassing analogues of biological relevant peptides, have been obtained in high purity. ...[more]

PMID: 34081467

Similar Datasets

Synthesis and Opioid Activity of Tyr1 -ψ[(Z)CF=CH]-Gly2 and Tyr1 -ψ[(S)/(R)-CF3 CH-NH]-Gly2 Leu-enkephalin Fluorinated Peptidomimetics.

Project description:We describe the design, synthesis, and opioid activity of fluoroalkene (Tyr1 -ψ[(Z)CF=CH]-Gly2 ) and trifluoroethylamine (Tyr1 -ψ[(S)/(R)-CF3 CH-NH]-Gly2 ) analogues of the endogenous opioid neuropeptide, Leu-enkephalin. The fluoroalkene peptidomimetic exhibited low nanomolar functional activity (5.0±2 nm and 60±15 nm for δ- and μ-opioid receptors, respectively) with a μ/δ-selectivity ratio that mimics that of the natural peptide. However, the trifluoroethylamine peptidomimetics, irrespective of stereochemistry, did not activate the opioid receptors, which suggest that bulky CF3 substituents are not tolerated at this position.

| S-EPMC5486982 | biostudies-literature

Colloids of Naked CH3NH3PbBr3 Perovskite Nanoparticles: Synthesis, Stability, and Thin Solid Film Deposition.

Project description:A novel preparation of lead halide, CH3NH3PbBr3, perovskite nanoparticle solid films from colloidal "naked" nanoparticles, that is, dispersible nanoparticles without any surfactant, is reported. The colloids are obtained by simply adding potassium ions, whose counterions are both more lipophilic and less coordinating than bromide ions, to the perovskite precursor solutions (CH3NH3Br/PbBr2 in dimethylformamide) following the reprecipitation strategy. The naked nanoparticles exhibit a low tendency to aggregate in solution, and they effectively self-assembled on a substrate by centrifugation of the colloid, leading to homogeneous nanoparticle solid films with arbitrary thickness. These results are expected to spur further the interest in lead halide perovskites due to the new opportunities offered by these films.

| S-EPMC6641344 | biostudies-literature

Gram-Scale Synthesis of Blue-Emitting CH3NH3PbBr3 Quantum Dots Through Phase Transfer Strategy.

Project description:Reprecipitation synthesis has been demonstrated to be a simple and convenient route to fabricate high quality perovskite quantum dots toward display applications, whereas the limited chemical yields (< 10%) and difficulty of purification limited its further application. In order to overcome this issue, we here report a modified emulsion synthesis by introducing phase transfer strategy, which achieving effective extraction of newly formed perovskite quantum dots into non-polar solvent and avoiding the degradation of perovskite quantum dots to a large extent. Based on this strategy, gram-scale CH3NH3PbBr3 quantum dots were fabricated in 10 mL (~0.02 mol/L) colloidal solution with chemical yields larger than 70%. The as fabricated CH3NH3PbBr3 quantum dots exhibit an emission peak of 453 nm and a full width at half maximum of only 14 nm. Moreover, electroluminescent devices based on blue emitting CH3NH3PbBr3 quantum dots were also explored with a maximum luminance of 32 cd/m2, showing potential applications in blue light emitting devices.

| S-EPMC6169035 | biostudies-literature

Hybrid Chlorides with Methylhydrazinium Cation: [CH3NH2NH2]CdCl3 and Jahn-Teller Distorted [CH3NH2NH2]CuCl3.

Project description:The synthesis, structural, phonon, optical, and magnetic properties of two hybrid organic-inorganic chlorides with monoprotonated methylhydrazinium cations (CH3NH2NH2+, MHy+), [CH3NH2NH2]CdCl3 (MHyCdCl3), and [CH3NH2NH2]CuCl3 (MHyCuCl3), are reported. In contrast to previously reported MHyMIICl3 (MII = Mn2+, Ni2+, and Co2+) analogues, neither compound undergoes phase transitions. The MHyCuCl3 has a crystal structure familiar to previous crystals composed of edge-shared 1D chains of the [CuCl5N] octahedra. MHyCuCl3 crystallizes in monoclinic P21/c symmetry with MHy+ cations directly linked to the Cu2+ ions. The MHyCdCl3 analogue crystallizes in lower triclinic symmetry with zig-zag chains of the edge-shared [CdCl6] octahedra. The absence of phase transitions is investigated and discussed. It is connected with slightly stronger hydrogen bonding between cations and the copper-chloride chains in MHyCuCl3 due to the strong Jahn-Teller effect causing the octahedra to elongate, resulting in a better fit of cations in the accessible space between chains. The absence of structural transformation in MHyCdCl3 is due to intermolecular hydrogen bonding between two neighboring MHy+ cations, which has never been reported for MHy+-based hybrid halides. Optical investigations revealed that the bandgaps in Cu2+ and Cd2+ analogues are 2.62 and 5.57 eV, respectively. Magnetic tests indicated that MHyCuCl3 has smeared antiferromagnetic ordering at 4.8 K.

| S-EPMC9865361 | biostudies-literature

Solid-phase synthesis of tetrahydropyridazinedione-constrained peptides.

Project description:The design and solid-phase synthesis of tetrahydropyridazine-3,6-dione (Tpd) peptidomimetics derived from backbone-aminated peptides is reported. The described protocol features the synthesis of chiral ?-hydrazino acids suitable for chemoselective incorporation into growing peptide chains. Acid-catalyzed cyclization to form the Tpd ring during cleavage affords the target peptidomimetics in good yield and purity. The scope of Tpd incorporation is demonstrated through the synthesis of constrained peptides featuring nucleophilic/electrophilic side chains and sterically encumbered ?-substituted hydrazino acid residues.

| S-EPMC4201324 | biostudies-literature

Solid-State Ligand-Exchange Fabrication of CH3NH3PbI3 Capped PbS Quantum Dot Solar Cells.

Project description:CH3NH3PbI3 capped PbS colloidal quantum dots have been successfully fabricated by solid-state ligand exchange from oleate and oleylamine capped PbS. The optimal solar cells made by layer-by-layer solution deposition give a high power conversion efficiency of 4.25% with an impressive short-circuit photocurrent density of 24.83 mA cm-2.

| S-EPMC5067684 | biostudies-literature

Experimental identification of aminomethanol (NH2CH2OH)-the key intermediate in the Strecker Synthesis.

Project description:The Strecker Synthesis of (a)chiral α-amino acids from simple organic compounds, such as ammonia (NH3), aldehydes (RCHO), and hydrogen cyanide (HCN) has been recognized as a viable route to amino acids on primordial earth. However, preparation and isolation of the simplest hemiaminal intermediate - the aminomethanol (NH2CH2OH)- formed in the Strecker Synthesis to even the simplest amino acid glycine (H2NCH2COOH) has been elusive. Here, we report the identification of aminomethanol prepared in low-temperature methylamine (CH3NH2) - oxygen (O2) ices upon exposure to energetic electrons. Isomer-selective photoionization time-of-flight mass spectrometry (PI-ReTOF-MS) facilitated the gas phase detection of aminomethanol during the temperature program desorption (TPD) phase of the reaction products. The preparation and observation of the key transient aminomethanol changes our perception of the synthetic pathways to amino acids and the unexpected kinetic stability in extreme environments.

| S-EPMC8770675 | biostudies-literature

Phase Stability and Electronic Properties of Hybrid Organic-Inorganic Perovskite Solid Solution (CH(NH2)2) x (CH3NH3)1-x Pb(Br y I1-y )3 as a Function of Composition.

Project description:Compositional mixing provides the means to maintain the structural stability of a hybrid organic-inorganic perovskite for efficient and robust photovoltaic applications. Here we present a theoretical, first-principles study of the electronic and energetic properties of the solid solution (CH(NH2)2) x (CH3NH3)1-x PbBr y I1-y , the mixing of two organic molecules with various orientations, formamidinium and methylammonium, and two halides, bromide and iodide. Our results show the variation in the band gap as a function of composition (x and y) provides several candidates that exceed the 27.5% Schockley-Queisser efficiency. The variation in the composition of hybrid perovskite shows specific regions where either the hexagonal or cubic phase dominates. We discuss the balance between the band gap and phase stability and indicate regions where the phase transition temperature between cubic and hexagonal phases is far from room temperature, indicating that these compositions are more robust at room temperature against phase transitions.

| S-EPMC9393887 | biostudies-literature

Plasma-Triggered CH4/NH3 Coupling Reaction for Direct Synthesis of Liquid Nitrogen-Containing Organic Chemicals.

Project description:Nitrogen-containing organic chemicals such as amines, amides, nitriles, and hydrazones are crucial in chemical and medical industries. This paper reports a direct synthesis of N,N-dimethyl cyanamide [(CH3)2NCN] and amino acetonitrile (NH2CH2CN) through a methane/ammonia (CH4/NH3) coupling reaction triggered by dielectric barrier discharge plasma, with by-products of hydrazine, amines, and hydrazones. The influence of CH4/NH3 molar ratio, feedstock residence time, and specific energy input on the CH4/NH3 plasma coupling reaction has been investigated and discussed. Under the optimized conditions, the productivities of (CH3)2NCN and NH2CH2CN reached 0.46 and 0.82 g·L-1·h-1, respectively, with 8.83% CH4 conversion. In addition, through combining the optical emission spectra diagnosis and the reaction results, a possible CH4/NH3 plasma coupling reaction mechanism has been proposed. This paper provides a potential fine application of CH4 and NH3 in green synthesis of liquid nitrogen-containing organic chemicals, such as nitriles, amines, amides, and hydrazones.

| S-EPMC6645566 | biostudies-literature

Site-selective solid phase synthesis of carbonylated peptides.

Project description:The aim of our research was to design an efficient method for the solid phase synthesis of carbonylated peptides. For this purpose, we designed and synthesized a fully protected derivative Fmoc-amino(2,5,5-trimetyhyl-1,3-dioxolan-2-yl)acetic acid (Fmoc-Atda-OH) of a novel unnatural amino acid (Thr(O)-2-amino-3-oxo-butanoic acid). To obtain the mentioned derivative, two synthetic strategies were investigated using different reagents for carbonyl protection, ethane-1,2-diol and 2,2-dimethyl-propane-1,3-diol. The racemization of oxidized threonine was also analyzed and discussed. We successfully carried out the solid phase synthesis of peptides containing a Thr(O) moiety using Fmoc-Atda-OH according to the standard Fmoc strategy. The application of the designed building block allows the synthesis of peptides containing D,L-Thr(O) residue, which may be used as models of oxidatively modified peptides which occur in biological systems and are related to many diseases.

| S-EPMC4458268 | biostudies-literature