Synonyms:2-amino-3-indolylpropanic acid;(2S)-2-azaniumyl-3-(1H-indol-3-yl)propanoate;3rzi;L-tryptophan zwitterion;3f3a;3qs4;3qs5;3qs6;SCHEMBL23141133;CHEBI:57912;(2S)-2-ammonio-3-(1H-indol-3-yl)propanoate
99%, *data from raw suppliers
Xi
There total 159 articles about (2S)-2-azaniumyl-3-(1H-indol-3-yl)propanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
Reference yield:
Reference yield:
Reference yield:
The research focuses on the development of an efficient peptide synthesis approach through a one-pot aziridine-mediated ligation-desulfurization strategy, specifically targeting the incorporation of phenylalanine and tryptophan residues into α-peptides. The methodology involves the regioselective ring-opening of aziridine-3-aryl-2-carboxylates with peptide thioacids, followed by desulfurization to yield the desired peptides. Key reactants include 3-phenyl- and 3-indolyl-substituted aziridin-2-carboxylates derivatives, synthesized from (2S,3R) β-hydroxy–α-azidophenylalanine and N-protected (2S,3R) β-hydroxy–α-azidotryptophan, and various peptide thioacids such as Boc-L-Val-SH. The experiments utilized solvents like DMF, DCM, THF, and ethanol, with reagents such as NaBH4/NiCl2.6H2O for the desulfurization step. The optimization of reaction conditions was conducted to maximize yields, and the scope of the method was explored with different peptide thioacids. Analyses included TLC monitoring, 1H NMR, and LC-HRMS to characterize intermediates and final products, confirming the regioselective formation of α-peptides with phenylalanine and tryptophan.
The research focuses on the development of antibacterial soft nanocomposites through the in situ synthesis of silver nanoparticles (AgNPs) within the self-assemblies of amino acid-based amphiphilic hydrogelators. The study aims to create materials effective against both Gram-positive and Gram-negative bacteria, without the need for external reducing or stabilizing agents. The experiments involved the synthesis of AgNPs using Tollens' reagent and amphiphilic hydrogelators derived from amino acids like tryptophan and tyrosine. The nanocomposites were characterized using UV-vis spectra, TEM, XRD, and TGA. The antibacterial activity was evaluated against various bacterial strains, and biocompatibility was assessed with mammalian cells, NIH3T3. The research also explored the influence of the head group charge and structure of the amphiphiles on the synthesis, stabilization of AgNPs, and the antibacterial activity of the nanocomposites. Notably, the soft nanocomposites demonstrated excellent antibacterial activity and considerable biocompatibility, showing potential for use in biomedical applications, including tissue engineering scaffolds.
This study presents an asymmetric synthetic approach for the production of enantiomerically pure 3-phenylaziridine-2-carboxylate 7, a key intermediate for the synthesis of α-phenyl-substituted cysteine, tryptophan, and serine derivatives. These novel amino acids are of great interest as they have the potential to enhance the bioactivity and selectivity of peptides by constraining their side chain conformations. The synthesis involves the Sharpless asymmetric dihydroxylation of trans-benzylcinnamate 1 to generate (2R,3S)-diol 2, which is then transformed through a series of reactions involving cyclic sulfite 3, cyclic sulfate 4, and azido alcohols 5 and 6 to ultimately afford the desired aziridine 7. Further reactions with nucleophiles such as 4-methoxybenzyl mercaptan, indole, and acetic acid form the target amino acid derivatives. The chemicals used in the study serve as starting materials, reagents, and solvents in the various synthetic steps, each playing a crucial role in the formation of intermediates and final products.
This research aimed to design and synthesize a series of N-acylhydrazone-linked, heterobivalent β-carboline derivatives derived from L-tryptophan. The purpose was to evaluate their in vitro cytotoxic activity against normal EA.HY926 cells and five cancer cell lines, as well as their in vivo antitumor efficacy in mice. The study concluded that compound 10e, with a 2,3,4,5,6-perfluorophenylmethyl group in the R9′-position, exhibited the most potent inhibitory activity against EA.HY926 cells and showed broad-spectrum cytotoxicity against various cancer cell lines. In vivo, compound 10e demonstrated significant antitumor activity and anti-metastatic potential, along with potent anti-angiogenetic effects. The chemicals used in the synthesis process included L-tryptophan, various aldehydes, ethanol, thionyl chloride (SOCl2), sulfur (S8), sodium hydride (NaH), N,N-dimethylformamide (DMF), and several substituted benzyl and alkyl halides, among others, to construct the heterobivalent β-carboline framework and introduce diverse substituents at different positions.
The research describes the successful total synthesis of the dimeric alkaloid amauromine, a compound of interest due to its unique structure and biological activity as a vasodilator. The purpose of the study was to achieve the first total synthesis of amauromine using a convergent synthetic route based on the thio-Claisen rearrangement reaction through a sulphonium salt, starting from L-tryptophan. Key chemicals used in the synthesis include L-tryptophan, phosphorus pentasulfide, methyl iodide, dicyclohexylcarbodiimide (DCC), N-hydroxysuccinimide (HOSu), potassium carbonate, prenyl bromide, titanium tetrachloride, and lithium aluminium hydride. The synthesis involved multiple steps, including oxidation, esterification, introduction of methylthio function, formation of the key intermediate diketopiperazine, thio-Claisen rearrangement, catalytic reduction, and reductive desulphurization. The final step involved concurrent cyclization and reductive desulphurization using TiCl4-LiAlH4 to obtain amauromine. The study concluded that the total synthesis was achieved with a yield of 15%, and the synthesized amauromine was identical to the natural compound in all respects, confirming the success of the synthetic route. This achievement supports the hypothesis on the mode of introduction of the inverted isoprene unit in related indole alkaloids and provides a potential pathway for the biosynthesis of amauromine.
What can I do for you?
Get Best Price
Total 8 Pictures about this product
