M.W=300-400 Archives - Ethers-buliding-blocks

Zheng, Mengjun team published research in Journal of Medicinal Chemistry in 2021 | 73724-45-5

73724-45-5, Fmoc-Ser-OH, also known as Fmoc-Ser-OH, is a useful research compound. Its molecular formula is C18H17NO5 and its molecular weight is 327.3 g/mol. The purity is usually 95%.
Fmoc-L-Ser-OH is a synthetic peptide that belongs to the group of glycopeptides. It is used as a model for such compounds and has been shown to have antimicrobial activity in vitro against gram-positive bacteria, especially Staphylococcus epidermidis. This compound was synthesized from 3-mercaptopropionic acid and chloride in the presence of hydroxyl groups and epidermal growth factor. The synthetic pathway can be divided into three steps: (1) condensation of 3-mercaptopropionic acid with hydrochloric acid to yield 3-mercaptoacrylic acid; (2) esterification of 3-mercaptoacrylic acid with glycine to form Fmoc-L-Ser; and (3) deprotection of Fmoc protecting group., Safety of Fmoc-Ser-OH

Ethers are a class of organic compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. 73724-45-5, formula is C18H17NO5, Name is Fmoc-Ser-OH.They have the general formula R–O–R′, where R and R′ represent the alkyl or aryl groups. Safety of Fmoc-Ser-OH.

Zheng, Mengjun;Cong, Wei;Peng, Haoran;Qing, Jie;Shen, Huaxing;Tang, Yaxin;Geng, Chenchen;Chen, Si;Zou, Yan;Zhang, Wei-Dong;Hu, Hong-Gang;Li, Xiang research published 《 Stapled Peptides Targeting SARS-CoV-2 Spike Protein HR1 Inhibit the Fusion of Virus to Its Cell Receptor》, the research content is summarized as follows. The pandemic of acute respiratory disease in 2019 caused by highly pathogenic and infectious SARS-CoV-2 has seriously endangered human public safety. The 6-helix bundle (6-HB) heptad repeat 1-heptad repeat 2 (HR1-HR2 complex) formation occurring in the process of spike protein-mediated membrane fusion could serve as a conserved and potential target for the design of fusion inhibitors. Based on the HR2 domain of 6-HB, we designed and synthesized 32 stapled peptides using an all-hydrocarbon peptide stapling strategy. Owing to the improved proteolytic stability and higher helical contents, the optimized stapled peptides termed SCH2-1-20 and SCH2-1-27 showed better inhibitory activities against pseudo and authentic SARS-CoV-2 compared to the linear counterpart. Of note, SCH2-1-20 and SCH2-1-27 were proved to interfere with S protein-mediated membrane fusion. Structural modeling indicated similar binding modes between SCH2-1-20 and the linear peptide. These optimized stapled peptides could serve as potent fusion inhibitors in treating and preventing SARS-CoV-2, and the corresponding SAR could facilitate further optimization.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Zheng, Yonggao team published research in European Journal of Organic Chemistry in 2021 | 73724-45-5

Formula: C18H17NO5, Fmoc-Ser-OH, also known as Fmoc-Ser-OH, is a useful research compound. Its molecular formula is C18H17NO5 and its molecular weight is 327.3 g/mol. The purity is usually 95%.
Fmoc-L-Ser-OH is a synthetic peptide that belongs to the group of glycopeptides. It is used as a model for such compounds and has been shown to have antimicrobial activity in vitro against gram-positive bacteria, especially Staphylococcus epidermidis. This compound was synthesized from 3-mercaptopropionic acid and chloride in the presence of hydroxyl groups and epidermal growth factor. The synthetic pathway can be divided into three steps: (1) condensation of 3-mercaptopropionic acid with hydrochloric acid to yield 3-mercaptoacrylic acid; (2) esterification of 3-mercaptoacrylic acid with glycine to form Fmoc-L-Ser; and (3) deprotection of Fmoc protecting group., 73724-45-5.

Ethers lack the hydroxyl groups of alcohols. Without the strongly polarized O―H bond, ether molecules cannot engage in hydrogen bonding with each other. 73724-45-5, formula is C18H17NO5, Name is Fmoc-Ser-OH. Ethers do have nonbonding electron pairs on their oxygen atoms, however, and they can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds. Formula: C18H17NO5.

Zheng, Yonggao;Zhao, Yanwei;Tao, Suyan;Li, Xingxing;Cheng, Xionglve;Jiang, Gangzhong;Wan, Xiaobing research published 《 Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite》, the research content is summarized as follows. In this work, the green esterification of carboxylic acids promoted by tert-Bu nitrite was well developed. This transformation was compatible with a broad range of substrates and exhibits excellent functional group tolerance. Various drugs and substituted amino acids were applicable to this reaction under near neutral conditions, with good to excellent yields.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Zhou, Zhixuan team published research in Journal of the American Chemical Society in 2022 | 73724-45-5

Ethers can again be classified into two varieties: if the alkyl or aryl groups are the same on both sides of the oxygen atom, 73724-45-5, formula is C18H17NO5, Name is Fmoc-Ser-OH. Then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. Product Details of C18H17NO5.

Zhou, Zhixuan;Maxeiner, Konrad;Moscariello, Pierpaolo;Xiang, Siyuan;Wu, Yingke;Ren, Yong;Whitfield, Colette J.;Xu, Lujuan;Kaltbeitzel, Anke;Han, Shen;Muecke, David;Qi, Haoyuan;Wagner, Manfred;Kaiser, Ute;Landfester, Katharina;Lieberwirth, Ingo;Ng, David Y. W.;Weil, Tanja research published 《 In Situ Assembly of Platinum(II)-Metallopeptide Nanostructures Disrupts Energy Homeostasis and Cellular Metabolism》, the research content is summarized as follows. Nanostructure-based functions are omnipresent in nature and essential for the diversity of life. Unlike small mols., which are often inhibitors of enzymes or biomimetics with established methods of elucidation, functions of nanoscale structures in cells are complex and can implicate system-level effects such as the regulation of energy and redox homeostasis. Herein, the authors design a Pt(II)-containing tripeptide that assembles into intracellular fibrillar nanostructures upon mol. rearrangement in the presence of endogenous H₂O₂. The formed nanostructures blocked metabolic functions, including aerobic glycolysis and oxidative phosphorylation, thereby shutting down ATP production As a consequence, ATP-dependent actin formation and glucose metabolite-dependent histone deacetylase activity are downregulated. Assembly-driven nanomaterials offer a rich avenue to achieve broad-spectrum bioactivities that could provide new opportunities in drug discovery.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Zhang, Chuanliang team published research in ACS Medicinal Chemistry Letters in 2021 | 73724-45-5

Synthetic Route of 73724-45-5, Fmoc-Ser-OH, also known as Fmoc-Ser-OH, is a useful research compound. Its molecular formula is C18H17NO5 and its molecular weight is 327.3 g/mol. The purity is usually 95%.
Fmoc-L-Ser-OH is a synthetic peptide that belongs to the group of glycopeptides. It is used as a model for such compounds and has been shown to have antimicrobial activity in vitro against gram-positive bacteria, especially Staphylococcus epidermidis. This compound was synthesized from 3-mercaptopropionic acid and chloride in the presence of hydroxyl groups and epidermal growth factor. The synthetic pathway can be divided into three steps: (1) condensation of 3-mercaptopropionic acid with hydrochloric acid to yield 3-mercaptoacrylic acid; (2) esterification of 3-mercaptoacrylic acid with glycine to form Fmoc-L-Ser; and (3) deprotection of Fmoc protecting group., 73724-45-5.

Zhang, Chuanliang;Wu, Lijuan;Liu, Xiaochun;Gao, Jiangming;Liu, Shan;Wu, Juan;Huang, Dingmin;Wang, Zhenwei;Su, Xianbin research published 《 Discovery of novel PTP1B inhibitors derived from the BH3 domain of proapoptotic Bcl-2 proteins with antidiabetic potency》, the research content is summarized as follows. BH3 peptide analogs are generally believed to exhibit great potency as cancer therapeutics via targeting antiapoptotic Bcl-2 proteins. Here, we describe the synthesis and identification of a new class of palmitoylated peptide BH3 analogs derived from the core region (h1-h4) of BH3 domains of proapoptotic Bcl-2 proteins and as alternative PTP1B inhibitors with antidiabetic potency in vitro and in vivo. PTP1B inhibitors are attractive for treatment of type 2 diabetes. We design the analogs using a simple lipidation approach and discovered novel lead analogs with promising antidiabetic potency in vitro and in vivo. The results presented here expanded the alternative target and function for the BH3 peptide analogs from one member Bim to other members of the proapoptotic Bcl-2 proteins and emphasize their therapeutic potential in T2DM. Furthermore, our findings may provide new proof of the regulatory function of Bcl-2 family proteins in mitochondrial nutrient and energy metabolism

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Zhang, Fa team published research in Molecular Metabolism in 2021 | 73724-45-5

Category: ethers-buliding-blocks, Fmoc-Ser-OH, also known as Fmoc-Ser-OH, is a useful research compound. Its molecular formula is C18H17NO5 and its molecular weight is 327.3 g/mol. The purity is usually 95%.
Fmoc-L-Ser-OH is a synthetic peptide that belongs to the group of glycopeptides. It is used as a model for such compounds and has been shown to have antimicrobial activity in vitro against gram-positive bacteria, especially Staphylococcus epidermidis. This compound was synthesized from 3-mercaptopropionic acid and chloride in the presence of hydroxyl groups and epidermal growth factor. The synthetic pathway can be divided into three steps: (1) condensation of 3-mercaptopropionic acid with hydrochloric acid to yield 3-mercaptoacrylic acid; (2) esterification of 3-mercaptoacrylic acid with glycine to form Fmoc-L-Ser; and (3) deprotection of Fmoc protecting group., 73724-45-5.

Zhang, Fa;Altindis, Emrah;Kahn, C. Ronald;DiMarchi, Richard D.;Gelfanov, Vasily research published 《 A viral insulin-like peptide is a natural competitive antagonist of the human IGF-1 receptor》, the research content is summarized as follows. Natural sources of mol. diversity remain of utmost importance as a reservoir of proteins and peptides with unique biol. functions. We recently identified such a family of viral insulin-like peptides (VILPs). We sought to advance the chem. methods in synthesis to explore the structure-function relationship within these VILPs, and the mol. basis for differential biol. activities relative to human IGF-1 and insulin.Optimized chem. methods in synthesis were established for a set of VILPs and related analogs. These modified forms included the substitution of select VILP chains with those derived from human insulin and IGF-1. Each peptide was assessed in vitro for agonism and antagonism at the human insulin and the human insulin-like growth factor 1 receptor (IGF-1R).We report here that one of these VILPs, lymphocystis disease virus-1 (LCDV1)-VILP, has the unique property to be a potent and full antagonist of the IGF-1R. We demonstrate the coordinated importance of the B- and C-chains of the VILP in regulating this activity. Moreover, mutation of the glycine following the first cysteine in the B-chain of IGF-1 to serine, in concert with substitution to the connecting peptide of LCDV1-VILP, converted native IGF-1 to a high potency antagonist.The results reveal novel aspects in ligand-receptor interactions at the IGF-1 receptor and identify a set of antagonists of potential medicinal importance.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Zhang, Feng team published research in Cell Reports in 2021 | 73724-45-5

Electric Literature of 73724-45-5, Fmoc-Ser-OH, also known as Fmoc-Ser-OH, is a useful research compound. Its molecular formula is C18H17NO5 and its molecular weight is 327.3 g/mol. The purity is usually 95%.
Fmoc-L-Ser-OH is a synthetic peptide that belongs to the group of glycopeptides. It is used as a model for such compounds and has been shown to have antimicrobial activity in vitro against gram-positive bacteria, especially Staphylococcus epidermidis. This compound was synthesized from 3-mercaptopropionic acid and chloride in the presence of hydroxyl groups and epidermal growth factor. The synthetic pathway can be divided into three steps: (1) condensation of 3-mercaptopropionic acid with hydrochloric acid to yield 3-mercaptoacrylic acid; (2) esterification of 3-mercaptoacrylic acid with glycine to form Fmoc-L-Ser; and (3) deprotection of Fmoc protecting group., 73724-45-5.

Zhang, Feng;Zhang, Yiran;Kong, Li;Luo, Huanhuan;Zhang, Yuezhou;Makila, Ermei;Salonen, Jarno;Hirvonen, Jouni T.;Zhu, Yueqi;Cheng, Yingsheng;Deng, Lianfu;Zhang, Hongbo;Kros, Alexander;Cui, Wenguo;Santos, Helder A. research published 《 Multistage signal-interactive nanoparticles improve tumor targeting through efficient nanoparticle-cell communications》, the research content is summarized as follows. Communication between biol. components is critical for homeostasis maintenance among the convergence of complicated bio-signals. For therapeutic nanoparticles (NPs), the general lack of effective communication mechanisms with the external cellular environment causes loss of homeostasis, resulting in deprived autonomy, severe macrophage-mediated clearance, and limited tumor accumulation. Here, we develop a multistage signal-interactive system on porous silicon particles through integrating the Self-peptide and Tyr-Ile-Gly-Ser-Arg (YIGSR) peptide into a hierarchical chimeric signaling interface with “don′t eat me” and “eat me” signals. This biochem. transceiver can act as both the signal receiver for amantadine to achieve NP transformation and signal conversion as well as the signal source to present different signals sequentially by reversible self-mimicking. Compared with the non-interactive controls, these signal-interactive NPs loaded with AS1411 and tanespimycin (17-AAG) as anticancer drugs improve tumor targeting 2.8-fold and tumor suppression 6.5-fold and showed only 51% accumulation in the liver with restricted hepatic injury.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Xuan, Maosong team published research in Colloids and Surfaces, A: Physicochemical and Engineering Aspects in 2021 | 73724-45-5

Application of C18H17NO5, Fmoc-Ser-OH, also known as Fmoc-Ser-OH, is a useful research compound. Its molecular formula is C18H17NO5 and its molecular weight is 327.3 g/mol. The purity is usually 95%.
Fmoc-L-Ser-OH is a synthetic peptide that belongs to the group of glycopeptides. It is used as a model for such compounds and has been shown to have antimicrobial activity in vitro against gram-positive bacteria, especially Staphylococcus epidermidis. This compound was synthesized from 3-mercaptopropionic acid and chloride in the presence of hydroxyl groups and epidermal growth factor. The synthetic pathway can be divided into three steps: (1) condensation of 3-mercaptopropionic acid with hydrochloric acid to yield 3-mercaptoacrylic acid; (2) esterification of 3-mercaptoacrylic acid with glycine to form Fmoc-L-Ser; and (3) deprotection of Fmoc protecting group., 73724-45-5.

Ethers feature bent C–O–C linkages. In dimethyl ether, the bond angle is 111° and C–O distances are 141 pm. 73724-45-5, formula is C18H17NO5, Name is Fmoc-Ser-OH. The barrier to rotation about the C–O bonds is low. The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3. Application of C18H17NO5.

Xuan, Maosong;Liang, Ju;Li, Junbo;Wu, Wenlan research published 《 Multi-functional lipopeptide micelles as a vehicle for curcumin delivery》, the research content is summarized as follows. Curcumin (CUR) is a kind of natural polyphenol with low aqueous solubility, poor bioavailability and favorable antitumor activity. In order to enhance anti-tumor activity and efficient delivery of CUR, an amphiphilic lipopeptide (C18H5R7RGDS, LP) containing H5R7RGDS heads and stearic acid (C18) tails was prepared by solid-phase peptide synthesis. Spherical LP micelles of ∼50 nm were self-assembled in PBS (pH 7.0) with good dispersion and significantly improved the aqueous solubility of CUR by 5400 times more than that of free CUR. The sequence of H5 in LP endowed the CUR-loaded LP micelles with good pH-responsive drug release behavior. In the case of pH 5.0, the electrostatic repulsion interaction among the ionized H5 fraction destroyed the structure of micelles, leading to significantly accelerated CUR release behavior. Hemolysis assay and proliferation inhibition test of normal cells confirmed apparently the excellent biocompatibility of LP. CUR-loaded LP micelles showed much higher cell growth inhibition on HepG2 cells and lower cytotoxicity on L02 cells than free CUR. With integrin-targeting sequence (RGD) and cell penetrating peptide (R8), LP micelles can more specifically and efficiently deliver CUR into integrin-overexpressed HepG2 cells than C18KR8 (LP-R1) and C18KRGDS (LP-R2) micelles. Combined with the enhanced drug solubility, distinctive pH-sensitive property and good tumor targeting, such LP micelles may have the clin. potential for tumor-targeting delivery.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Yao, Guiyang team published research in Journal of the American Chemical Society in 2021 | 73724-45-5

Yao, Guiyang;Knittel, Caroline H.;Kosol, Simone;Wenz, Marius T.;Keller, Bettina G.;Gruss, Hendrik;Braun, Alexandra C.;Lutz, Christian;Hechler, Torsten;Pahl, Andreas;Suessmuth, Roderich D. research published 《 Iodine-mediated tryptathionine formation facilitates the synthesis of amanitins》, the research content is summarized as follows. Synthetic methods on the macrocyclization of peptides are of high interest since they facilitate the synthesis of various types of potentially bioactive compounds, e.g. addressing targets like protein-protein-interactions. Herein, we report on an efficient method to construct tryptathionine-cross-links in peptides between the amino acids Trp and Cys. This reaction not only is the basis for the total synthesis of the death cap toxin α-amanitin but also provides rapid access to various new amanitin analogs. This study for the first time presents a systematic compilation of structure-activity relations (SAR) of amatoxins with regard to RNA polymerase II inhibition and cytotoxicity with one amanitin derivative of superior RNAP II inhibition. The present approach paves the way for the synthesis of structurally diverse amatoxins as future payloads for antibody-toxin conjugates in cancer therapy.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Yin, Huawu team published research in Journal of the American Chemical Society in 2021 | 73724-45-5

Yin, Huawu;Zhou, Xiuman;Huang, Yen-Hua;King, Gordon J.;Collins, Brett M.;Gao, Yanfeng;Craik, David J.;Wang, Conan K. research published 《 Rational Design of Potent Peptide Inhibitors of the PD-1:PD-L1 Interaction for Cancer Immunotherapy》, the research content is summarized as follows. Peptides have potential to be developed into immune checkpoint inhibitors, but the target interfaces are difficult to inhibit. Here, we explored an approach to mimic the binding surface of PD-1 to design inhibitors. Mimicking native PD-1 resulted in a mimetic with no activity. However, mimicking an affinity-optimized PD-1 resulted in the peptide mimetic MOPD-1 that displayed nanomolar affinity to PD-L1 and could inhibit PD-1:PD-L1 interactions in both protein- and cell-based assays. Mutagenesis and structural characterization using NMR spectroscopy and X-ray crystallog. revealed that binding residues from the high affinity PD-1 are crucial for the bioactivity of MOPD-1. Furthermore, MOPD-1 was extremely stable in human serum and inhibited tumor growth in vivo, suggesting it has potential for use in cancer immunotherapy. The successful design of an inhibitor of PD-1:PD-L1 using the mimicry approach described herein illustrates the value of placing greater emphasis on optimizing the target interface before inhibitor design and is an approach that could have broader utility for the design of peptide inhibitors for other complex protein-protein interactions.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Yu, Ziqiang team published research in Journal of Peptide Science in 2022 | 73724-45-5

Yu, Ziqiang;Tang, Hua;Cong, Wei;Gao, Fei;Li, Huaqiang;Hu, Honggang;Wang, Xiaoyan;He, Shipeng research published 《 Hydrocarbon stapling modification of peptide Alyteserin-2a: Discovery of novel stapled peptide antitumor agents》, the research content is summarized as follows. Alyteserin-2a (ILGKLLSTAAGLLSNL-NH₂) is isolated from the skin exudates of midwife toad and has a wide range of biol. applications. However, the use of alyteserin-2a as an antitumor agent is limited due to its structural flexibility. In this study, a series of stapled peptides were prepared through hydrocarbon stapling modification without destroying the key residues, and their chem. and biol. properties were further evaluated for enhancing the application potential of alyteserin-2a in the field of antitumor drugs development. Among them, alyteserin-2a-Sp3 displayed significant improvement in helicity levels, protease resistance, and antitumor activity compared to that of the template peptide alyteserin-2a, indicating that alyteserin-2a-Sp3 had a potential to become a lead compound for the development of novel antitumor drugs. This study confirms the important effect of hydrocarbon stapling strategy on the secondary structure, hydrolase stability, and biol. activity of alyteserin-2a.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem