M.W=300-400 Archives - Page 2 of 38 - Ethers-buliding-blocks

Whitely, Chelsi team published research in Tetrahedron Letters in 2022 | 73724-45-5

Reference 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.

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. Reference of 73724-45-5.

Whitely, Chelsi;Li, Yangmei research published 《 One-pot high-throughput synthesis of N3-substituted 5-arylidene-2-thiohydantoin amides and acids》, the research content is summarized as follows. A one-pot high-throughput solid-phase method for the synthesis of N3-substituted 5-arylidene-2-thiohydantoin amide and acid has been developed. A tandem ring-closure and ring-open pathway is proposed as the mechanism of forming the two products.

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

Wierzbicka, Magdalena team published research in Journal of Organic Chemistry in 2021 | 73724-45-5

Wierzbicka, Magdalena;Waliczek, Mateusz;Dziadecka, Anna;Stefanowicz, Piotr research published 《 One-pot cyclization and cleavage of peptides with N-terminal cysteine via the N,S-acyl shift of the N-2-[thioethyl]glycine residue》, the research content is summarized as follows. We developed a one-pot method for peptide cleavage from a solid support via the N,S-acyl shift of N-2-[thioethyl]glycine and transthioesterification using external thiols to produce cyclic peptides through native chem. self-ligation with the N-terminal cysteine. The feasibility of this methodol. is validated by the syntheses of model short peptides, including a tetrapeptide, the bicyclic sunflower trypsin inhibitor SFTI-1, and rhesus Θ-defensin RTD-1. Synthesis of the whole peptide precursor can be fully automated and proceeds without epimerization or dimerization.

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

Wolf, Philipp team published research in Journal of Peptide Science 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.

Wolf, Philipp;Beck-Sickinger, Annette G. research published 《 The ring size of monocyclic ET-1 controls selectivity and signaling efficiency at both endothelin receptor subtypes》, the research content is summarized as follows. Cardiovascular diseases (CVDs) like hypertension are a major cause for death worldwide. In the cardiovascular tissue, the endothelin system-consisting of the receptor subtypes A (ET_AR) and B (ET_BR) and the mixed agonist endothelin 1 (ET-1)-is a major key player in the regulation of vascular tone and blood pressure. Tight control of this system is required to maintain homeostasis; otherwise, the endothelin system can cause severe CVDs like pulmonary artery hypertension. The high sequence homol. between both receptor subtypes limits the development of novel and selective ligands. Identification of small differences in receptor-ligand interactions and determination of selectivity constraints are crucial to fine-tune ligand properties and subsequent signaling events. Here, we report on novel ET-1 analogs and their detailed pharmacol. characterization. We generated simplified ET-1-derived monocyclic peptides to provide an accessible synthesis route. By detailed in vitro characterization, we demonstrated that both G protein signaling and the subsequent arrestin recruitment of activated ET_BR remain intact, whereas activation of the ET_AR depends on the intramol. ring size. Increasing of the intramol. ring structure reduces activity at the ET_AR and shifts the peptide toward ET_BR selectivity. All ET-1 analogs displayed efficient ET_BR-mediated signaling by G protein activation and arrestin 3 recruitment. Our study provides in-depth characterization of the ET-1/ET_AR and ET-1/ET_BR interactions, which has the potential for future development of endothelin-based drugs for CVD treatment. By identification of Lys⁹ for selective labeling, novel analogs for peptide-mediated shuttling by ET-1 are proposed.

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

Wood, Thomas M. 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., Formula: C18H17NO5

Wood, Thomas M.;Slingerland, Cornelis J.;Martin, Nathaniel I. research published 《 A convenient chemoenzymatic preparation of chimeric macrocyclic peptide antibiotics with potent activity against gram-negative pathogens》, the research content is summarized as follows. The continuing rise of antibiotic resistance, particularly among Gram-neg. pathogens, threatens to undermine many aspects of modern medical practice. To address this threat, novel antibiotics that utilize unexploited bacterial targets are urgently needed. Over the past decade, a number of studies have highlighted the antibacterial potential of macrocyclic peptides that target Gram-neg. outer membrane proteins (OMPs). Recently, it was reported that the antibacterial activities of OMP-targeting macrocyclic peptidomimetics of the antimicrobial peptide protegrin-1 are dramatically enhanced upon linking to polymyxin E nonapeptide (PMEN). In this study, we describe a convergent, chemoenzymic route for the convenient preparation of such conjugates. Specifically, we investigated the use of both amide bond formation and azide-alkyne ligation for connecting an OMP-targeting macrocyclic peptide to a PMEN building block (obtained by enzymic degradation of polymyxin E). The conjugates obtained via both approaches display potent antibacterial activity against a range of Gram-neg. pathogens including multi-drug-resistant isolates.

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

Wu, Yaqi team published research in Bioconjugate Chemistry in 2021 | 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. Category: ethers-buliding-blocks.

Wu, Yaqi;Li, Cong;Fan, Shihui;Zhao, Yibing;Wu, Chuanliu research published 《 Fast and selective reaction of 2-benzylacrylaldehyde with 1,2-aminothiol for stable N-terminal cysteine modification and peptide cyclization》, the research content is summarized as follows. N-terminal cysteine (Cys)-specific reactions have been exploited for protein and peptide modifications. However, existing reactions for N-terminal Cys suffer from low reaction rate, unavoidable side reactions, or poor stability for reagents or products. Herein we report a fast, efficient, and selective conjugation between 2-benzylacrylaldehyde (BAA) and 1,2-aminothiol, which involves multistep reactions including aldimine condensation, Michael addition, and reduction of imine by NaBH₃CN. This conjugation proceeds with a rate constant of ~2700 M^-1 s^-1 under neutral condition at room temperature to produce a pair of seven-membered ring diastereoisomers, which are stable under neutral and acidic conditions. This method enables the selective modifications of the N-terminal Cys residue without interference from the internal Cys and lysine residues, providing a useful alternative to existing approaches for site-specific peptide or protein modifications and synthesis of cyclic peptides.

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

Wu, Ye team published research in Chinese Chemical Letters in 2021 | 73724-45-5

SDS of cas: 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.

Ethers do have nonbonding electron pairs on their oxygen atoms, 73724-45-5, formula is C18H17NO5, Name is Fmoc-Ser-OH. The ability to form hydrogen bonds with other compounds makes ethers particularly good solvents for a wide variety of organic compounds and a surprisingly large number of inorganic compounds. SDS of cas: 73724-45-5.

Wu, Ye;Zou, Yan;Sun, Lingling;Garzino-Demo, Alfredo;Hu, Honggang;Zhang, Weidong;Li, Xiang research published 《 Peptide stapling with the retention of double native side-chains》, the research content is summarized as follows. All-hydrocarbon stapling strategy has been widely applied for enhancing the proteolytic stability of peptides. However, two major tech. hurdles to some extent limit the development of stapled peptides for therapeutic usage: rational selection of the stapling sites and the corresponding deletion of the native side chains. Previously we described the development of the olefin-terminated amino acids with the retention of native side chains and successfully applied them in the synthesis of hydrocarbon stapled peptides with single side-chain retention. Here, we explored the feasibility and effectiveness of hydrocarbon stapling strategy characterized as double side-chains retention. Modeled after a lengthy human immunodeficiency virus-1 (HIV-1) fusion inhibitor SC34EK, Leuⁱ, Serⁱ⁺⁴ and Lysⁱ, Leuⁱ⁺⁴ stapled peptides with the retention of double side-chains were effectively obtained. Our complementary study provided a convenient alternative to address where to install the staple in sequence for conventional all-hydrocarbon peptide stapling. Furthermore, this method not only conferred conformational reinforcement for SC34EK with high α-helicity and protease resistance, but also preserved the structural characteristic (key peripheral residues, charge and solubility) of the linear peptide to the maximum, which are crucial for anti-HIV-1 activity.

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

Xia, Yiran team published research in Chinese Chemical Letters in 2022 | 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.

Xia, Yiran;Hao, Aiyou;Xing, Pengyao research published 《 Fmoc-protected amino acids as luminescent and circularly polarized luminescence materials based on charge transfer interaction》, the research content is summarized as follows. Fluorenylmethyloxycarbonyl (Fmoc)-protected amino acids are effective building blocks in self-assembled architectures at hierarchical levels, which however show limited luminescent properties and chiroptical activities. Here we introduce a charge-transfer strategy to build two-component luminescent materials with emerged circularly polarized luminescence properties. A library of Fmoc-amino acids was built, which selectively form charge-transfer complexes with the electron-deficient acceptor. Embedding in amorphous polymer matrix or phys. grinding could trigger the charge-transfer luminescence with adjusted wavelengths in a general manner. X-ray diffraction results suggest the multiple binding modes between donor and acceptor. And, the solution-processed coassembly could selectively exhibit circularly polarized luminescence with high dissymmetry g-factors. This work illustrates a noncovalent charge-transfer strategy to construct luminescent and chiroptical organic composites based on the easy-accessible and economic chiral N-terminal aromatic amino acids.

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

Wang, Shuai team published research in Journal of Medicinal Chemistry in 2021 | 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. Computed Properties of 73724-45-5.

Wang, Shuai;Zhu, Xiaopeng;Zhangsun, Manqi;Wu, Yong;Yu, Jinpeng;Harvey, Peta J.;Kaas, Quentin;Zhangsun, Dongting;Craik, David J.;Luo, Sulan research published 《 Engineered Conotoxin Differentially Blocks and Discriminates Rat and Human α7 Nicotinic Acetylcholine Receptors》, the research content is summarized as follows. The α7 nicotinic acetylcholine receptor (nAChR) is present in the central nervous system and plays an important role in cognitive function and memory. α-Conotoxin LvIB, identified from genomic DNA of Conus lividus, its three isomers and four globular isomer analogs were synthesized and screened at a wide range of nAChR subtypes. One of the analogs, amidated [Q1G,ΔR14]LvIB, was found to be a potent blocker of rat α7 nAChRs. Importantly, it differentiates between α7 nAChRs of human (IC₅₀: 1570 nM) and rat (IC₅₀: 97 nM). Substitutions between rat and human α7 nAChRs at three key mutation sites revealed that no single mutant could completely change the activity profile of amidated [Q1G,ΔR14]LvIB. Rather, we found that the combined influence of Gln141, Asn184, and Lys186 determines the α7 nAChR species specificity of this peptide. This engineered α4/4 conotoxin has potential applications as a template for designing ligands to selectively block human α7 nAChRs.

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

Wang, Siyao team published research in Angewandte Chemie, International Edition in 2022 | 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. SDS of cas: 73724-45-5.

Wang, Siyao;Zhou, QingQing;Zhang, Xiaheng;Wang, Ping research published 《 Site-selective itaconation of complex peptides by photoredox catalysis》, the research content is summarized as follows. Site-selective peptide functionalization provides a straightforward and cost-effective access to diversify peptides for biol. studies. Among many existing non-invasive peptide conjugations methodologies, photoredox catalysis has emerged as one of the powerful approaches for site-specific manipulation on native peptides. Herein, we report a highly N-termini-specific method to rapidly access itaconated peptides and their derivatives through a combination of transamination and photoredox conditions. This strategy exploits the facile reactivity of peptidyl-dihydropyridine in the complex peptide settings, complementing existing approaches for bioconjugations with excellent selectivity under mild conditions. Distinct from conventional methods, this method utilizes the highly reactive carbamoyl radical derived from a peptidyl-dihydropyridine. In addition, this itaconated peptide can be further functionalized as a Michael acceptor to access the corresponding peptide-protein conjugate.

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

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

HPLC of Formula: 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.

Wang, Zhengning;Wang, Xuewei;Wang, Penghui;Zhao, Junfeng research published 《 Allenone-mediated racemization/epimerization-free peptide bond formation and its application in peptide synthesis》, the research content is summarized as follows. Allenone has been identified as a highly effective peptide coupling reagent for the first time. The peptide bond was formed with an α-carbonyl vinyl ester as the key intermediate, the formation and subsequent aminolysis of which proceed spontaneously in a racemization-/epimerization-free manner. The allenone coupling reagent not only is effective for the synthesis of simple amides and dipeptides but is also amenable to peptide fragment condensation and solid-phase peptide synthesis (SPPS). The robustness of the allenone-mediated peptide bond formation was showcased incisively by the synthesis of carfilzomib, which involved a rare racemization-/epimerization-free N to C peptide elongation strategy. Furthermore, the successful synthesis of the model difficult peptide ACP (65-74) on a solid support suggested that this method was compatible with SPPS. This method combines the advantages of conventional active esters and coupling reagents, while overcoming the disadvantages of both strategies. Thus, this allenone-mediated peptide bond formation strategy represents a disruptive innovation in peptide synthesis.

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