Tag: M.W=400-450

Rochon, Kristina published the artcilePreparation and Evaluation at the Delta Opioid Receptor of a Series of Linear Leu-Enkephalin Analogues Obtained by Systematic Replacement of the Amides, Application of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, the publication is ACS Chemical Neuroscience (2013), 4(8), 1204-1216, database is CAplus and MEDLINE.

Leu-enkephalin analogs, in which the amide bonds were sequentially and systematically replaced either by ester or N-Me amide bonds, were prepared using classical organic chem. as well as solid-phase peptide synthesis (SPPS). The peptidomimetics were characterized using competition binding, ERK1/2 phosphorylation, receptor internalization, and contractility assays to evaluate their pharmacol. profile over the delta opioid receptor (DOPr). The lipophilicity (LogD_7.4) and plasma stability of the active analogs were also measured. The results here revealed that the last amide bond can be successfully replaced by either an ester or an N-Me amide bond without significantly decreasing the biol. activity of the corresponding analogs when compared to Leu-enkephalin. The peptidomimetics with an N-Me amide function between residues Phe and Leu were found to be more lipophilic and more stable than Leu-enkephalin. Findings from the present study further revealed that the hydrogen-bond donor properties of the fourth amide of Leu-enkephalin are not important for its biol. activity on DOPr. In addition, the results showed that the systematic replacement of amide bonds by isosteric functions represents an efficient way to design and synthesize novel peptide analogs with enhanced stability. In conclusion, the authors suggest that such a strategy can also be useful to study the biol. roles of amide bonds.

ACS Chemical Neuroscience 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

Jin, Kang published the artcileSynthesis and structure-activity relationship of teixobactin analogues via convergent Ser ligation, Formula: C25H23NO4, the publication is Bioorganic & Medicinal Chemistry (2017), 25(18), 4990-4995, database is CAplus and MEDLINE.

Convergent Ser/Thr ligation has been used to prepare a series of teixobactin analogs (28 in total) to establish a structure-activity relationship of teixobactin. anti-bacterial evaluations of these synthetic analogs have revealed the critical amino acid residues and the sites tolerable of modifications. These studies will shed lights on the further development of teixobactin analogs with improved antibacterial activities.

Bioorganic & 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, Formula: C25H23NO4.

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

Deng, Yuqing published the artcileSelection of DNA-Encoded Dynamic Chemical Libraries for Direct Inhibitor Discovery, Synthetic Route of 77128-73-5, the publication is Angewandte Chemie, International Edition (2020), 59(35), 14965-14972, database is CAplus and MEDLINE.

Dynamic combinatorial libraries (DCLs) is a powerful tool for ligand discovery in biomedical research; however, the application of DCLs has been hampered by their low diversity. Recently, the concept of DNA encoding has been employed in DCLs to create DNA-encoded dynamic libraries (DEDLs); however, all current DEDLs are limited to fragment identification, and a challenging process of fragment linking is required after selection. The authors report an anchor-directed DEDL approach that can identify full ligand structures from large-scale DEDLs. This method is also able to convert unbiased libraries into focused ones targeting specific protein classes. The authors demonstrated this method by selecting DEDLs against five proteins, and novel inhibitors were identified for all targets. Notably, several selective BD1/BD2 inhibitors were identified from the selections against bromodomain 4 (BRD4), an important anti-cancer drug target. This work may provide a broadly applicable method for inhibitor discovery.

Angewandte Chemie, International Edition 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, Synthetic Route of 77128-73-5.

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

Sarnowski, Matthew P. published the artcileSynthesis and β-sheet propensity of constrained N-amino peptides, Computed Properties of 77128-73-5, the publication is Bioorganic & Medicinal Chemistry (2018), 26(6), 1162-1166, database is CAplus and MEDLINE.

The stabilization of β-sheet secondary structure through peptide backbone modification represents an attractive approach to protein mimicry. Here, we present strategies toward stable β-hairpin folds based on peptide strand N-amination. Novel pyrazolidinone and tetrahydropyridazinone dipeptide constraints were introduced via on-resin Mitsunobu cyclization between α-hydrazino acid residues and a serine or homoserine side chain. Acyclic and cyclic N-amino peptide building blocks were then evaluated for their effect on β-hairpin stability in water using a GB1-derived model system. Our results demonstrate the strong β-sheet stabilizing effect of the peptide N-amino substituent, and provide useful insights into the impact of covalent dipeptide constraint on β-sheet folding.

Bioorganic & 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, Computed Properties of 77128-73-5.

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

Roodbeen, Renee published the artcileMicrowave Heating in the Solid-Phase Synthesis of N-Methylated Peptides: When Is Room Temperature Better?, Name: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, the publication is European Journal of Organic Chemistry (2012), 2012(36), 7106-7111, database is CAplus.

The N-methylation of backbone amides in synthetic peptides is an important method for improving properties such as bioavailability, stability, as well as structural preferences, and is thus an attractive design strategy. However, the synthesis of N-methylated peptides can be challenging as the nucleophile in the acylation step is a sterically hindered secondary amine. In this study, the authors have systematically evaluated the use of microwave heating, different coupling conditions and the role of steric effects on coupling yields. First, the coupling reagent providing the highest yields was identified by a series of test N-acylation reactions on a selected peptide sequence. Secondly, a comparison of the coupling temperature, i.e., room temperature vs. microwave heating, with the optimal coupling reagent was performed. Finally, under the optimal conditions, a comprehensive study employing a set of sterically hindered N-methylated amino acids was conducted. Interestingly, incorporation of Fmoc-Arg(Pbf)-OH proceeded with higher yields at room temperature than at elevated temperature as a result of intramol. Arg lactam formation, which competes with intermol. amide bond formation. Fmoc-Arg(Boc)₂-OH provided even lower coupling yields, due to the complete formation of the Arg lactam product. These studies have led to a robust, rapid, easy and high-yielding microwave-assisted method using COMU for the incorporation of Fmoc amino acids into challenging, sterically hindered N-methylated amino acid residues in a peptide sequence without the use of harsh reagents.

European Journal of Organic 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, Name: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid.

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

Garland, Keira published the artcileOptimization of globomycin analogs as novel gram-negative antibiotics, COA of Formula: C25H23NO4, the publication is Bioorganic & Medicinal Chemistry Letters (2020), 30(20), 127419, database is CAplus and MEDLINE.

Discovery of novel classes of Gram-neg. antibiotics with activity against multi-drug resistant infections is a critical unmet need. As an essential member of the lipoprotein biosynthetic pathway, lipoprotein signal peptidase II (LspA) is an attractive target for antibacterial drug discovery, with the natural product inhibitor globomycin offering a modestly-active starting point. Informed by structure-based design, the globomycin depsipeptide was optimized to improve activity against E. coli. Backbone modifications, together with adjustment of physicochem. properties, afforded potent compounds with good in vivo pharmacokinetic profiles. Optimized compounds such as (I) (E. coli MIC 3.1μM) and (II) (E. coli MIC 0.78μM) demonstrate broad spectrum activity against gram-neg. pathogens and may provide opportunities for future antibiotic discovery.

Bioorganic & Medicinal Chemistry Letters 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, COA of Formula: C25H23NO4.

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

Wang, Zi-Long published the artcileStructure-Based Optimization of Multifunctional Agonists for Opioid and Neuropeptide FF Receptors with Potent Nontolerance Forming Analgesic Activities, Name: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, the publication is Journal of Medicinal Chemistry (2016), 59(22), 10198-10208, database is CAplus and MEDLINE.

The opioid and neuropeptide FF pharmacophore-containing chimeric peptide 0 (BN-9) was recently developed and produced potent nontolerance forming analgesia. In this study, 11 analogs of 0 were designed and synthesized. An in vitro cAMP assay demonstrated that these analogs behaved as multifunctional agonists at both opioid and NPFF receptors. In mouse tail-flick test, most of the analogs produced potent nontolerance forming antinociception. Notably, 11 (DN-9) was 33-fold more potent than 0 at analgesic effects, which was mediated by μ- and κ-opioid receptors. In addition, 11 also produced powerful analgesic effects in the formalin pain and CFA-induced chronic inflammatory pain models. Strikingly, following its repeated administration for 6 days, 11 did not produce antinociceptive tolerance in the tail-flick test and CFA-induced pain model. The present work indicates that it is reasonable to design multifunctional peptide ligands for opioid and NPFF receptors in a single mol. producing effective nontolerance forming antinociception.

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 C6H3ClFNO2, Name: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid.

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

Sato, Ryota published the artcileInvestigation for the cyclization efficiency of linear tetrapeptides: Synthesis of tentoxin B and dihydrotentoxin, Computed Properties of 77128-73-5, the publication is Tetrahedron (2018), 74(42), 6173-6181, database is CAplus.

Investigation of the cyclization efficiency of N-Me linear tetrapeptides using a mol. modeling study and chem. synthesis is described. The linear peptide with two N-Me groups, MeAla-Leu-MePhe-Gly, forms γ-turn like conformation with the amine at N-terminus and the carbonyl at C-terminus in closer proximity to give the desired cyclic tetrapeptide, dihydrotentoxin. In addition, synthesis of tentoxin B by the combination of Fmoc solid-phase peptide synthesis (Fmoc = 9-fluorenylmethoxycarbonyl) and cyclization in solution phase has been reported. An unusual amino acid, an L-N-methyl-β-hydroxyphenylalanine derivative, which was assembled on solid support, was prepared from Et cinnamate. Cyclic tetrapeptide formation and cleavage of benzyl ether were optimized with DIPCI/HOBt/DIPEA and Et₃SiH/Pd(OH)₂, 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, Computed Properties of 77128-73-5.

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

Misu, Ryosuke published the artcileDevelopment of Novel Neurokinin 3 Receptor (NK3R) Selective Agonists with Resistance to Proteolytic Degradation, Formula: C25H23NO4, the publication is Journal of Medicinal Chemistry (2014), 57(20), 8646-8651, database is CAplus and MEDLINE.

Neurokinin B (NKB) regulates the release of gonadotropin-releasing hormone (GnRH) via activation of the neurokinin-3 receptor (NK3R). We evaluated the biol. stability of NK3R selective agonists to develop novel NK3R agonists to regulate reproductive functions. On the basis of degradation profiles, several peptidomimetic derivatives were designed. The modification of senktide with (E)-alkene dipeptide isostere generated a novel potent NK3R agonist with high stability and prolonged bioactivity.

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, Formula: C25H23NO4.

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

Noguchi, Taro published the artcileStructure-activity relationship study of neurokinin-3 receptor agonists, SDS of cas: 77128-73-5, the publication is Peptide Science (2013), 189-190, database is CAplus.

A symposium report. Neurokinin B (NKB) is a member of the tachykinin peptide family. NKB and the cognate receptor, neurokinin-3 receptor (NK3R), are involved in the secretion of the gonadotropin releasing hormone (GnRH) by kisspeptin neurons. Our SAR study demonstrated that NK3R-selectivity was improved by modifications of Phe⁵ and Val⁷ in NKB and the corresponding residues in the tachykinin peptides.

Peptide Science 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, SDS of cas: 77128-73-5.

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