Tag: M.W=400-450

Xie, Yong published the artcileSynthesis, Biological Activity, and Conformational Study of N-Methylated Allatostatin Analogues Inhibiting Juvenile Hormone Biosynthesis, Recommanded Product: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, the publication is Journal of Agricultural and Food Chemistry (2015), 63(11), 2870-2876, database is CAplus and MEDLINE.

An allatostatin (AST) neuropeptide mimic (H17) is a potential insect growth regulator, which inhibits the production of juvenile hormone (JH) by the corpora allata. To determine the effect of conformation of novel AST analogs and their ability to inhibit JH biosynthesis, eight insect AST analogs were synthesized using H17 as the lead compound by N-methylation scanning, which is a common strategy for improving the biol. properties of peptides. A bioassay using JH production by corpora allata of the cockroach Diploptera punctata indicated that single N-methylation mimics (analogs 1-4) showed more activity than double N-methylation mimics (analogs 5-8). Especially, analogs 1 and 4 showed roughly equivalent activity to that of H17, with IC₅₀ values of 5.17 × 10^-8 and 6.44 × 10^-8 M, resp. Mol. modeling based on NMR data showed that the conformation of analogs 1 and 4 seems to be flexible, whereas analogs 2 and 3 showed a type IV β-turn. This flexible linear conformation was hypothesized to be a new important and indispensable structural element beneficial to the activity of AST mimics.

Journal of Agricultural and Food Chemistry published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C12H17NO2, Recommanded Product: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Hickey, Jennifer L. published the artcilePassive Membrane Permeability of Macrocycles Can Be Controlled by Exocyclic Amide Bonds, Product Details of C25H23NO4, the publication is Journal of Medicinal Chemistry (2016), 59(11), 5368-5376, database is CAplus and MEDLINE.

We have developed a strategy for synthesizing passively permeable peptidomimetic macrocycles. The cyclization chem. centers on using aziridine aldehydes in a multicomponent reaction with peptides and isocyanides. The linker region in the resulting product contains an exocyclic amide positioned α to the peptide backbone, an arrangement that is not found among natural amino acids. This amide provides structural rigidity within the cyclic peptidomimetic and promotes the creation of a stabilizing intramol. hydrogen bonding network. This exocyclic control element also contributes to the increased membrane permeability exhibited by multicomponent-derived macrocycles with respect to their homodetic counterparts. The exocyclic control element is employed along with a strategic placement of N-Me and D-amino acids to produce passively permeable peptides, which contain multiple polar residues. This strategy should be applicable in the pursuit of synthesizing therapeutically relevant macrocycles.

Journal of Medicinal Chemistry published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C25H23NO4, Product Details of C25H23NO4.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Ishiyama, Haruaki published the artcileEnantioselective total synthesis of eudistomidins G, H, and I, Formula: C25H23NO4, the publication is Tetrahedron (2012), 68(31), 6186-6192, database is CAplus.

Asym. first total synthesis of eudistomidins G, H, and I, tetrahydro-β-carboline alkaloids from the Okinawan marine tunicate Eudistoma glaucus, has been accomplished with the Bischler-Napieralski reaction and the Noyori catalytic asym. hydrogen-transfer reaction. The absolute configurations of eudistomidins G, H, and I were confirmed from comparison of the ¹H and ¹³C NMR, and CD spectral data of synthetic and natural eudistomidins G, H, and I, resp.

Tetrahedron published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C25H23NO4, Formula: C25H23NO4.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Kreutzer, Adam G. published the artcileStabilization, Assembly, and Toxicity of Trimers Derived from Aβ, Category: ethers-buliding-blocks, the publication is Journal of the American Chemical Society (2017), 139(2), 966-975, database is CAplus and MEDLINE.

Oligomers of the β-amyloid peptide Aβ have emerged as important contributors to neurodegeneration in Alzheimer’s disease. Mounting evidence suggests that Aβ trimers and higher-order oligomers derived from trimers have special significance in the early stages of Alzheimer’s disease. Elucidating the structures of these trimers and higher-order oligomers is paramount for understanding their role in neurodegeneration. This paper describes the design, synthesis, X-ray crystallog. structures, and biophys. and biol. properties of two stabilized trimers derived from the central and C-terminal regions of Aβ. These triangular trimers are stabilized through three disulfide crosslinks between the monomer subunits. The X-ray crystallog. structures reveal that the stabilized trimers assemble hierarchically to form hexamers, dodecamers, and annular pore-like structures. Solution-phase biophys. studies reveal that the stabilized trimers assemble in solution to form oligomers that recapitulate some of the higher-order assemblies observed crystallog. The stabilized trimers share many of the biol. characteristics of oligomers of full-length Aβ, including toxicity toward a neuronally derived human cell line, activation of caspase-3 mediated apoptosis, and reactivity with the oligomer-specific antibody A11. These studies support the biol. significance of the triangular trimer assembly of Aβ β-hairpins and may offer a deeper understanding of the mol. basis of Alzheimer’s disease.

Journal of the American Chemical Society published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C25H23NO4, Category: ethers-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Sun, Pengli published the artcileSynthesis of Fmoc-N-methyl-L-phenylalanine with microwave-assisted, Safety of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, the publication is Guangzhou Huagong (2012), 40(10), 64-65, database is CAplus.

Fmoc-protected N-methyl-L-phenylalanine was synthesized under the presence of trifluoroacetic acid and anhydrous aluminum chloride as catalyzer and the triethylsilane as reduction, in which the Fmoc-protected L-phenylalanine was used as original material, passing though the generated intermediate 5-oxazolidinone with microwave assisted heating method. The result showed that using the microwave assisted heating method, the reaction time greatly reduced and the mean total yield increased to 82%, and the composite catalyzer of trifluoroacetic acid and anhydrous aluminum chloride could avoid generating the byproduct Fmoc-Tic-OH and save original material.

Guangzhou Huagong published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C2H8Cl2N4S2, Safety of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Zhang, Mengna published the artcileDevelopment of Multifunctional and Orally Active Cyclic Peptide Agonists of Opioid/Neuropeptide FF Receptors that Produce Potent, Long-Lasting, and Peripherally Restricted Antinociception with Diminished Side Effects, Application In Synthesis of 77128-73-5, the publication is Journal of Medicinal Chemistry (2021), 64(18), 13394-13409, database is CAplus and MEDLINE.

We previously reported that a multifunctional opioid/neuropeptide FF receptor agonist, DN-9, achieved peripherally restricted analgesia with reduced side effects. To develop stable and orally bioavailable analogs of DN-9, eight lactam-bridged cyclic analogs of DN-9 between positions 2 and 5 were designed, synthesized, and biol. evaluated. In vitro cAMP assays revealed that these analogs, except 7, were multifunctional ligands that activated opioid and neuropeptide FF receptors. Analog 1 exhibited improved potency for κ-opioid and NPFF₂ receptors. All analogs exhibited potent, long-lasting, and peripherally restricted antinociception in the tail-flick test without tolerance development after s.c. administration and produced oral analgesia. Oral administration of the optimized compound analog 1 exhibited powerful, peripherally restricted antinociceptive effects in mouse models of acute, inflammatory, and neuropathic pain. Remarkably, orally administered analog 1 had no significant side effects, such as tolerance, dependence, constipation, or respiratory depression, at effective analgesic doses.

Journal of Medicinal Chemistry published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C7H5Br2F, Application In Synthesis of 77128-73-5.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Zhang, Hang published the artcileStructure-Activity Relationship Studies of the Cyclic Depsipeptide Natural Product YM-254890, Targeting the G_q Protein, SDS of cas: 77128-73-5, the publication is ChemMedChem (2017), 12(11), 830-834, database is CAplus and MEDLINE.

Extracellular signals perceived by G protein-coupled receptors are transmitted via G proteins, and subsequent intracellular signaling cascades result in a plethora of physiol. responses. The natural product cyclic depsipeptides YM-254890 and FR900359 are the only known compounds that specifically inhibit signaling mediated by the G_q subfamily. In this study we exploit a newly developed synthetic strategy for this compound class in the design, synthesis, and pharmacol. evaluation of eight new analogs of YM-254890. These structure-activity relationship studies led to the discovery of three new analogs, YM-13, YM-14, and YM-18, which displayed potent and selective G_q inhibitory activity. This provides pertinent information for the understanding of the G_q inhibitory mechanism by this class of compounds and importantly provides a pathway for the development of labeled YM-254890 analogs.

ChemMedChem published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C37H30ClIrOP2, SDS of cas: 77128-73-5.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Proctor, Angela published the artcileDevelopment of a Peptidase-Resistant Substrate for Single-Cell Measurement of Protein Kinase B Activation, Recommanded Product: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, the publication is Analytical Chemistry (Washington, DC, United States) (2012), 84(16), 7195-7202, database is CAplus and MEDLINE.

An iterative design strategy using three criteria was utilized to develop a peptidase-resistant substrate peptide for protein kinase B. Libraries of peptides possessing non-native amino acids were screened for time to 50% phosphorylation, degradation half-life within a lysate, and appearance of a dominant fragment. The lead peptide possessed a half-life of 92 ± 7 and 16 ± 2 min in HeLa and LNCaP cytosolic lysates, resp., representing a 4.6- and 2.7-fold lifetime improvement over that of the starting peptide. The redesigned peptide possessed a 4.5-fold improvement in phosphorylation efficiency compared to the starting peptide. The same peptide fragments were formed when the lead peptide was incubated in a lysate or loaded into single cells although the fragments formed in significantly different ratios suggesting that distinct peptidases metabolized the peptide in the two preparations The rate of peptide degradation and phosphorylation was on average 0.1 ± 0.2 zmol pg^-1 s^-1 and 0.04 ± 0.08 zmol pg^-1 s^-1, resp., for single LNCaP cells loaded with 4 ± 8 μM of peptide. Peptidase-resistant kinase substrates should find widespread utility in both lysate-based and single-cell assays of kinase activity.

Analytical Chemistry (Washington, DC, United States) published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C25H23NO4, Recommanded Product: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Proctor, Angela published the artcileMetabolism of peptide reporters in cell lysates and single cells, Application of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, the publication is Analyst (Cambridge, United Kingdom) (2012), 137(13), 3028-3038, database is CAplus and MEDLINE.

The stability of an Abl kinase substrate peptide in a cytosolic lysate and in single cells was characterized. In the cytosolic lysate, the starting peptide was metabolized at an average initial rate of 1.7 ± 0.3 zmol pg^-1 s^-1 with a t_1/2 of 1.3 min. Five different fragments formed over time; however, a dominant cleavage site was identified. Multiple rational design cycles were utilized to develop a lead peptide with a phenylalanine and alanine replaced by an (N-methyl)phenylalanine and isoleucine, resp., to attain cytosolic peptidase resistance while maintaining Abl substrate efficacy. This lead peptide possessed a 15-fold greater lifetime in the cytosolic lysate while attaining a 7-fold improvement in k_cat as an Abl kinase substrate compared to the starting peptide. However, when loaded into single cells, the starting peptide and lead peptide possessed nearly identical degradation rates and an altered pattern of fragmentation relative to that in cell lysates. Preferential accumulation of a fragment with cleavage at an Ala-Ala bond in single cells suggested that dissimilar peptidases act on the peptides in the lysate vs. single cells. A design strategy for peptide stabilization, analogous to that demonstrated for the lysate, should be effective for stabilization in single cells.

Analyst (Cambridge, United Kingdom) published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C25H23NO4, Application of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Ramalho, Suelem D. published the artcileSynthesis, racemic X-ray crystallographic, and permeability studies of bioactive orbitides from Jatropha species, HPLC of Formula: 77128-73-5, the publication is Journal of Natural Products (2018), 81(11), 2436-2445, database is CAplus and MEDLINE.

Orbitides are small cyclic peptides with a diverse range of therapeutic bioactivities. They are produced by many plant species, including those of the Jatropha genus. Here, the objective was to provide new structural information on orbitides to complement the growing knowledge base on orbitide sequences and activities by focusing on three Jatropha orbitides: ribifolin, pohlianin C, and jatrophidin. To determine three-dimensional structures, racemic crystallog., an emerging structural technique that enables rapid crystallization of biomols. by combining equal amounts of the two enantiomers, was used. The high-resolution structure of ribifolin (0.99 Å) was elucidated from its racemate and showed it was identical to the structure crystallized from its L-enantiomer only (1.35 Å). Racemic crystallog. was also used to elucidate high-resolution structures of pohlianin C (1.20 Å) and jatrophidin (1.03 Å), for which there was difficulty forming crystals without using racemic mixtures The structures were used to interpret membrane permeability data in PAMPA and a Caco-2 cell assay, showing they had poor permeability. Overall, the results show racemic crystallog. can be used to obtain high-resolution structures of orbitides and is useful when enantiopure samples are difficult to crystallize or solution structures from NMR are of low resolution

Journal of Natural Products published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C25H23NO4, HPLC of Formula: 77128-73-5.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem