M.W=400-450 | - Page 5 of 13 - Indole Building Blocks

Takeuchi, Aoi team published research on Chemistry – An Asian Journal in 2021 | 35737-15-6

35737-15-6, Nalpha-FMOC-L-Tryptophan,also known as Fmoc-Trp-OH， is a useful research compound. Its molecular formula is C26H22N2O4 and its molecular weight is 426.5 g/mol. The purity is usually 95%.
Nα-Fmoc-L-Tryptophan is an N-Fmoc protected form of L-Tryptophan (T947210). L-Tryptophan is an essential amino acid that is important for cell proliferation and the biosynthesis of proteins. It is a precursor to Serotonin (HCl: S274980), a neurotransmitter that compound that aids in sleep and mental state. L-Tryptophan is also thought to cause eosinophilia-myalgia syndrome.
Fmoc-Trp-OH is an amino acid derivative
Fmoc-L-Trp-OH is an amide that contains a low bioavailability and inhibits the transfer of amino acids to ribosomes. It has been shown to inhibit the growth of cancer cells in cell culture and to have antimicrobial activity. Fmoc-L-Trp-OH is synthesized by reacting Naphthalene with glycine, followed by hydrolysis of the ester group under trifluoroacetic acid. The product is then conjugated with a polypeptide. This method of synthesis was developed as a way to produce peptides that are difficult to synthesize using solid-phase chemistry., Formula: C26H22N2O4

Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. 35737-15-6, formula is C26H22N2O4, Name is Fmoc-Trp-OH. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings. Formula: C26H22N2O4.

Takeuchi, Aoi;Itoh, Hiroaki;Inoue, Masayuki research published 《 ¹⁸O/¹⁶O-Encoding strategy for microscale stereochemical determination of peptidic natural products》, the research content is summarized as follows. The demand for more efficient methods of establishing the undetermined stereochemistries of peptidic natural products continues unabated. A new method for microscale stereochem. determination was devised by integrating solid-phase synthesis, split-and-mix randomization, ¹⁸O/¹⁶O-encoding of D/L-configurations, tandem mass spectrometry, and biol. evaluation. Here we applied gramicidin A as the mol. for a blind test. Gramicidin A and its 31 diastereomers were randomly prepared in microgram scale with ¹⁸O/¹⁶O-stereochem. encoding and subjected to MS/MS-structural determination and cytotoxicity assay. Only the parent gramicidin A was selected from among the 32 stereoisomers, validating the high reliability of the present strategy.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Tamaribuchi, Kenya team published research on Advanced Synthesis & Catalysis in 2022 | 35737-15-6

Related Products of 35737-15-6, Nalpha-FMOC-L-Tryptophan,also known as Fmoc-Trp-OH， is a useful research compound. Its molecular formula is C26H22N2O4 and its molecular weight is 426.5 g/mol. The purity is usually 95%.
Nα-Fmoc-L-Tryptophan is an N-Fmoc protected form of L-Tryptophan (T947210). L-Tryptophan is an essential amino acid that is important for cell proliferation and the biosynthesis of proteins. It is a precursor to Serotonin (HCl: S274980), a neurotransmitter that compound that aids in sleep and mental state. L-Tryptophan is also thought to cause eosinophilia-myalgia syndrome.
Fmoc-Trp-OH is an amino acid derivative
Fmoc-L-Trp-OH is an amide that contains a low bioavailability and inhibits the transfer of amino acids to ribosomes. It has been shown to inhibit the growth of cancer cells in cell culture and to have antimicrobial activity. Fmoc-L-Trp-OH is synthesized by reacting Naphthalene with glycine, followed by hydrolysis of the ester group under trifluoroacetic acid. The product is then conjugated with a polypeptide. This method of synthesis was developed as a way to produce peptides that are difficult to synthesize using solid-phase chemistry., 35737-15-6.

Indole, first isolated in 1866, has the molecular formula C8H7N, and it is commonly synthesized from phenylhydrazine and pyruvic acid, 35737-15-6, formula is C26H22N2O4, Name is Fmoc-Trp-OH. although several other procedures have been discovered.Indole is a colourless solid having a pleasant fragrance in highly dilute solutions. It melts at 52.5° C (126.5° F). Related Products of 35737-15-6.

Tamaribuchi, Kenya;Tian, Jiaqi;Akagawa, Kengo;Kudo, Kazuaki research published 《 Enantioselective nitro-Michael addition catalyzed by N-terminal guanidinylated helical peptide》, the research content is summarized as follows. Enantioselective Michael addition of β-dicarbonyl compounds toward nitroalkenes were realized by using an immobilized, N-terminal-guanidinylated peptide, H₂N-C(=NH)-Trp-Trp-(Leu-Leu-Aib)₃-PEG-PS-resin (Aib=2-aminoisobutyric acid), as catalyst. Viable nucleophiles were acetylacetone, di-Me malonate, and β-ketoesters. The electrophiles include the β-nitrostryrenes with various substituents on the benzene ring and the aliphatic nitroalkenes. Sterically congested α-ethoxycarbonyl-β-nitrostryrene also successfully reacted. The resin-supported catalyst could be recycled for five times.

Tang, Rui team published research on Bioconjugate Chemistry in 2021 | 35737-15-6

Computed Properties of 35737-15-6, Nalpha-FMOC-L-Tryptophan,also known as Fmoc-Trp-OH， is a useful research compound. Its molecular formula is C26H22N2O4 and its molecular weight is 426.5 g/mol. The purity is usually 95%.
Nα-Fmoc-L-Tryptophan is an N-Fmoc protected form of L-Tryptophan (T947210). L-Tryptophan is an essential amino acid that is important for cell proliferation and the biosynthesis of proteins. It is a precursor to Serotonin (HCl: S274980), a neurotransmitter that compound that aids in sleep and mental state. L-Tryptophan is also thought to cause eosinophilia-myalgia syndrome.
Fmoc-Trp-OH is an amino acid derivative
Fmoc-L-Trp-OH is an amide that contains a low bioavailability and inhibits the transfer of amino acids to ribosomes. It has been shown to inhibit the growth of cancer cells in cell culture and to have antimicrobial activity. Fmoc-L-Trp-OH is synthesized by reacting Naphthalene with glycine, followed by hydrolysis of the ester group under trifluoroacetic acid. The product is then conjugated with a polypeptide. This method of synthesis was developed as a way to produce peptides that are difficult to synthesize using solid-phase chemistry., 35737-15-6.

In addition to indoleacetic acid, indigo, and tryptophan, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. 35737-15-6, formula is C26H22N2O4, Name is Fmoc-Trp-OH. The best-known group of these compounds is the indole alkaloids, members of which have been isolated from plants representing more than 30 families. Computed Properties of 35737-15-6.

Tang, Rui;Song, Yue;Shi, Mengzhen;Jiang, Zherui;Zhang, Ling;Xiao, Yao;Tian, Yuan;Zhou, Shaobing research published 《 Rational design of a dual-targeting natural toxin-like bicyclic peptide for selective bioenergetic blockage in cancer cells》, the research content is summarized as follows. Stapled α-helical peptides emerge as one of the attractive peptidomimetics which can efficiently penetrate the cell membrane to access intracellular targets. However, the incorporation of a highly lipophilic cross-link may lead to nonspecific membrane toxicity in certain cases. Here, we report a new class of thioether-tethered bicyclic α-helical peptide to mimic the highly constrained loop-helix structure of natural toxins with the dual-targeting ability for both cell-surface receptors and intracellular targets. The thioether cross-links are introduced to replace the redox-sensitive disulfide bonds in natural toxins via a photoinduced thiol-yne reaction followed by macrolactamization. As a proof of concept, α_Vβ₃ integrin targeting ligand was grafted into one of the macrocycles in the bicyclic scaffold, while a mitochondria-targeting proapoptotic motif was introduced into the other macrocycle stabilized by an i, i + 7 alkyl thioether cross-link to recapitulate its α-helical conformation. The obtained dual-targeting bicyclic α-helical BIRK peptides showed highly stable α-helical conformation in the presence of denaturants or under high temperature Notably, BIRK peptides could induce selective cell death in α_Vβ₃ integrin-pos. B16F10 cells by interfering with the bioenergetic functions of mitochondria. This work provides a new avenue to design and stabilize α-helical peptides in a highly constrained bicyclic loop-helix scaffold with dual functionality.

Todorov, Petar team published research on New Journal of Chemistry in 2022 | 35737-15-6

Todorov, Petar;Peneva, Petia;Georgieva, Stela;Tchekalarova, Jana;Rangelov, Miroslav;Todorova, Nadezhda research published 《 Synthesis and characterization of new 5,5′-dimethyl- and 5,5′-diphenylhydantoin-conjugated hemorphin derivatives designed as potential anticonvulsant agents》, the research content is summarized as follows. Herein, the synthesis and characterization of some novel N-modified hybrid analogs of hemorphins containing a C-5 substituted hydantoin residue as potential anticonvulsants and for the blockade of sodium channels are presented. Their structure-property relationships are highlighted by electrochem. and Fourier transform IR spectroscopy (FT-IR) anal. methods. The lipophilicity and mol. docking of voltage-gated sodium channels were also determined The new series of 5,5-dimethyl- and 5,5-diphenylhydantoin-conjugated hemorphin derivatives were obtained as C-terminal amides via solid-phase peptide synthesis, an Fmoc-strategy using 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethylaminium tetrafluoroborate (TBTU). The anticonvulsant activity of the hybrid-peptides (0.25, 0.5 and 1 μg) was tested by maximal electroshock (MES) and 6 Hz psychomotor seizure tests using male ICR mice. None of the compounds tested showed neurotoxicity in the rotarod test. The reference drug phenytoin was used as a pos. control. The most active compound Ph-5 showed 100% efficacy against the 6 Hz-induced psychomotor seizures at a dose of 1.0 μg and tonic seizures in the MES test at a lower dose of 0.5 μg. This analog of VV-hemorphin-5 contained a 5,5-diphenylhydantoin residue at the N-terminus and a hydrophobic Val-Val-Tyr-Pro-Trp-Thr-Gln-CONH₂ amino acid sequence of the peptide mol. The quant. data for the 6 Hz test demonstrated that the peptide Ph-5 exhibited a median ED (ED50) value of 0.358 μg and PI >13.97, and ED50 of 0.25 μg and PI >20.35 in the MES test, resp. Results from the docking study suggest that the neuropeptide Ph-5 is a potent inhibitor of sodium channels, and blockade of voltage-gated sodium channels could be the mechanism of action of the hybrid-peptide derivatives with anticonvulsant activity.

Tran, Kien team published research on Journal of Medicinal Chemistry in 2021 | 35737-15-6

Tran, Kien;Van Den Hauwe, Robin;Sainsily, Xavier;Couvineau, Pierre;Cote, Jerome;Simard, Louise;Echevarria, Marco;Murza, Alexandre;Serre, Alexandra;Theroux, Lea;Saibi, Sabrina;Haroune, Lounes;Longpre, Jean-Michel;Lesur, Olivier;Auger-Messier, Mannix;Spino, Claude;Bouvier, Michel;Sarret, Philippe;Ballet, Steven;Marsault, Eric research published 《 Constraining the Side Chain of C-Terminal Amino Acids in Apelin-13 Greatly Increases Affinity, Modulates Signaling, and Improves the Pharmacokinetic Profile》, the research content is summarized as follows. Side-chain-constrained amino acids are useful tools to modulate the biol. properties of peptides. In this study, we applied side-chain constraints to apelin-13 (Ape13) by substituting the Pro12 and Phe13 positions, affecting the binding affinity and signaling profile on the apelin receptor (APJ). The residues 1Nal, Trp, and Aia were found to be beneficial substitutions for Pro12, and the resulting analogs displayed high affinity for APJ (K_i 0.08-0.18 nM vs Ape13 K_i 0.7 nM). Besides, constrained (D-Tic) or α,α-disubstituted residues (Db_zg; D-α-Me-Tyr(OBn)) were favorable for the Phe13 position. Compounds 47 (Pro12-Phe13 replaced by Aia-Phe, K_i 0.08 nM) and 53 (I) (Pro12-Phe13 replaced by 1Nal-Db_zg, K_i 0.08 nM) are the most potent Ape13 analogs activating the Gα₁₂ pathways (53, EC₅₀ Gα₁₂ 2.8 nM vs Ape13, EC₅₀ 43 nM) known to date, displaying high affinity, resistance to ACE2 cleavage as well as improved pharmacokinetics in vitro (t_1/2 5.8-7.3 h in rat plasma) and in vivo.

Vamisetti, Ganga B. team published research on Angewandte Chemie, International Edition in 2021 | 35737-15-6

Application In Synthesis of 35737-15-6, Nalpha-FMOC-L-Tryptophan,also known as Fmoc-Trp-OH， is a useful research compound. Its molecular formula is C26H22N2O4 and its molecular weight is 426.5 g/mol. The purity is usually 95%.
Nα-Fmoc-L-Tryptophan is an N-Fmoc protected form of L-Tryptophan (T947210). L-Tryptophan is an essential amino acid that is important for cell proliferation and the biosynthesis of proteins. It is a precursor to Serotonin (HCl: S274980), a neurotransmitter that compound that aids in sleep and mental state. L-Tryptophan is also thought to cause eosinophilia-myalgia syndrome.
Fmoc-Trp-OH is an amino acid derivative
Fmoc-L-Trp-OH is an amide that contains a low bioavailability and inhibits the transfer of amino acids to ribosomes. It has been shown to inhibit the growth of cancer cells in cell culture and to have antimicrobial activity. Fmoc-L-Trp-OH is synthesized by reacting Naphthalene with glycine, followed by hydrolysis of the ester group under trifluoroacetic acid. The product is then conjugated with a polypeptide. This method of synthesis was developed as a way to produce peptides that are difficult to synthesize using solid-phase chemistry., 35737-15-6.

Vamisetti, Ganga B.;Meledin, Roman;Nawatha, Mickal;Suga, Hiroaki;Brik, Ashraf research published 《 The development of a fluorescence-based competitive assay enabled the discovery of dimeric cyclic peptide modulators of ubiquitin chains》, the research content is summarized as follows. Development of modulators targeting specific interactions of ubiquitin-based conjugates with their partners is a formidable task since it requires a suitable screening assay and homogeneous ubiquitin conjugates. We developed a novel high-throughput strategy for screening ligands for Lys48-linked tetraubiquitin chain in a relatively simple, fast, and affordable manner. This approach combined with a state-of-the-art toolbox of chem. protein synthesis and a specially optimized Cys deprotection protocol enabled us to design highly potent, Lys48-linked tetraubiquitin chain selective “next generation” dimeric peptide modulators. The dimeric peptide exhibited cancer cell permeability and induced cell death with higher efficiency compared to its monocyclic analog. These features make our dimeric peptide a promising candidate for further studies using in vivo models. Our assay can be adopted for other various ubiquitin chains in their free or anchored forms as well as conjugates for Ub-like modifiers.

Soerensen, Kasper K. team published research on ChemBioChem in 2021 | 35737-15-6

Soerensen, Kasper K.;Mishra, Narendra K.;Paprocki, Maciej P.;Mehrotra, Amit;Jensen, Knud J. research published 《 High-Performance Reversed-Phase Flash Chromatography Purification of Peptides and Chemically Modified Insulins》, the research content is summarized as follows. Preparative reversed-phase HPLC is the established method for the purification of peptides, but has significant limitations. We systematically investigated the use of high-performance reversed-phase flash chromatog. (HPFC) to rapidly purify laboratory-scale quantities of crude, synthetic peptides and chem. modified insulins. We demonstrated these methods for a diverse set of peptides, including short, medium, and long peptides. Depending on the purity profile of the peptide, HPFC can be used either as the sole purification method, or as a pre-purification method prior to final HPLC purification Furthermore, HPFC is suitable for the purification of peptides that are not fully in solution We provide guidelines for the HPFC of synthetic peptides and small proteins, including the choice of columns, eluents, and gradients. We believe that HPFC is a valuable alternative to HPLC purification of peptides and small proteins.

Reja, Rahi M. team published research on Journal of the American Chemical Society in 2022 | 35737-15-6

Category: indole-building-block, Nalpha-FMOC-L-Tryptophan,also known as Fmoc-Trp-OH， is a useful research compound. Its molecular formula is C26H22N2O4 and its molecular weight is 426.5 g/mol. The purity is usually 95%.
Nα-Fmoc-L-Tryptophan is an N-Fmoc protected form of L-Tryptophan (T947210). L-Tryptophan is an essential amino acid that is important for cell proliferation and the biosynthesis of proteins. It is a precursor to Serotonin (HCl: S274980), a neurotransmitter that compound that aids in sleep and mental state. L-Tryptophan is also thought to cause eosinophilia-myalgia syndrome.
Fmoc-Trp-OH is an amino acid derivative
Fmoc-L-Trp-OH is an amide that contains a low bioavailability and inhibits the transfer of amino acids to ribosomes. It has been shown to inhibit the growth of cancer cells in cell culture and to have antimicrobial activity. Fmoc-L-Trp-OH is synthesized by reacting Naphthalene with glycine, followed by hydrolysis of the ester group under trifluoroacetic acid. The product is then conjugated with a polypeptide. This method of synthesis was developed as a way to produce peptides that are difficult to synthesize using solid-phase chemistry., 35737-15-6.

Reja, Rahi M.;Wang, Wenjian;Lyu, Yuhan;Haeffner, Fredrik;Gao, Jianmin research published 《 Lysine-Targeting Reversible Covalent Inhibitors with Long Residence Time》, the research content is summarized as follows. We report a new reversible lysine conjugation that features a novel diazaborine product and much slowed dissociation kinetics in comparison to the previously known iminoboronate chem. Incorporating the diazaborine-forming warhead RMR1 to a peptide ligand gives potent and long-acting reversible covalent inhibitors of the staphylococcal sortase. The efficacy of sortase inhibition is demonstrated via biochem. and cell-based assays. A comparative study of RMR1 and an iminoboronate-forming warhead highlights the significance and potential of modulating bond dissociation kinetics in achieving long-acting reversible covalent inhibitors.

Rol, Alvaro team published research on Nature Communications in 2021 | 35737-15-6

Recommanded Product: Fmoc-Trp-OH, Nalpha-FMOC-L-Tryptophan,also known as Fmoc-Trp-OH， is a useful research compound. Its molecular formula is C26H22N2O4 and its molecular weight is 426.5 g/mol. The purity is usually 95%.
Nα-Fmoc-L-Tryptophan is an N-Fmoc protected form of L-Tryptophan (T947210). L-Tryptophan is an essential amino acid that is important for cell proliferation and the biosynthesis of proteins. It is a precursor to Serotonin (HCl: S274980), a neurotransmitter that compound that aids in sleep and mental state. L-Tryptophan is also thought to cause eosinophilia-myalgia syndrome.
Fmoc-Trp-OH is an amino acid derivative
Fmoc-L-Trp-OH is an amide that contains a low bioavailability and inhibits the transfer of amino acids to ribosomes. It has been shown to inhibit the growth of cancer cells in cell culture and to have antimicrobial activity. Fmoc-L-Trp-OH is synthesized by reacting Naphthalene with glycine, followed by hydrolysis of the ester group under trifluoroacetic acid. The product is then conjugated with a polypeptide. This method of synthesis was developed as a way to produce peptides that are difficult to synthesize using solid-phase chemistry., 35737-15-6.

Rol, Alvaro;Todorovski, Toni;Martin-Malpartida, Pau;Escola, Anna;Gonzalez-Rey, Elena;Aragon, Eric;Verdaguer, Xavier;Valles-Miret, Mariona;Farrera-Sinfreu, Josep;Puig, Eduard;Fernandez-Carneado, Jimena;Ponsati, Berta;Delgado, Mario;Riera, Antoni;Macias, Maria J. research published 《 Structure-based design of a Cortistatin analogue with immunomodulatory activity in models of inflammatory bowel disease》, the research content is summarized as follows. Ulcerative colitis and Crohn′s disease are forms of inflammatory bowel disease whose incidence and prevalence are increasing worldwide. These diseases lead to chronic inflammation of the gastrointestinal tract as a result of an abnormal response of the immune system. Recent studies positioned Cortistatin, which shows low stability in plasma, as a candidate for IBD treatment. Here, using NMR structural information, we design five Cortistatin analogs adopting selected native Cortistatin conformations in solution One of them, A5, preserves the anti-inflammatory and immunomodulatory activities of Cortistatin in vitro and in mouse models of the disease. Addnl., A5 displays an increased half-life in serum and a unique receptor binding profile, thereby overcoming the limitations of the native Cortistatin as a therapeutic agent. This study provides an efficient approach to the rational design of Cortistatin analogs and opens up new possibilities for the treatment of patients that fail to respond to other therapies.

Sakamoto, Kentarou team published research on Bioconjugate Chemistry in 2021 | 35737-15-6

Sakamoto, Kentarou;Michibata, Junya;Hirai, Yusuke;Ide, Akiko;Ikitoh, Asuka;Takatani-Nakase, Tomoka;Futaki, Shiroh research published 《 Potentiating the Membrane Interaction of an Attenuated Cationic Amphiphilic Lytic Peptide for Intracellular Protein Delivery by Anchoring with Pyrene Moiety》, the research content is summarized as follows. We previously reported an approach for intracellular protein delivery by attenuating membrane-lytic activity of cationic amphiphilic peptides on cell surfaces. HAad is one such peptides that cytosolically delivers proteins of interest, including antibodies, by stimulating their endosomal escape. Addnl., HAad elicits ruffling of cell membrane, accompanied by transient membrane permeabilization, allowing for the efficient cytosolic translocation of proteins. In this study, we prepared a conjugate of HAad with pyrenebutyric acid as a membrane-anchoring unit (pBu-HAad). pBu-HAad demonstrated protein delivery into cells with only 1/20 concentration of HAad. However, the conjugates with cholesteryl hemisuccinate and aliphatic fatty acids (C = 3, 6, and 10) did not yield such marked effects. The results of time-course and inhibitor studies suggest that the membrane anchoring of HAad by a pyrene moiety leads to enhanced peptide-membrane interaction and to loosen lipid packing, thus facilitating cytosolic translocation through membranes.