Synonyms:(2S)-2-azaniumyl-3-methylbutanoate;L-Val;L-valine zwitterion;L-(+)-valine;(S)-(+)-valine;CHEBI:57762;L-2-Amino-3-methylbutyric acid;(2S)-2-ammonio-3-methylbutanoate;(2S)-2-azaniumyl-3-methyl-butanoate;H-Val-OH;A837443
98% *data from raw suppliers
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There total 390 articles about (2S)-2-azaniumyl-3-methylbutanoate 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: 100.0%
Reference yield: 57.4%
Reference yield:
L-valine methylester hydrochloride
The research focuses on the development of novel bifunctional ureas and thioureas immobilized on sulfonylpolystryrene as recoverable and reusable organocatalysts for the enantioselective aza-Henry reaction under solvent-free conditions. The activity and stereoselection of these catalysts depend on the length of the tether connecting the active site and the polymer, with the catalyst derived from 1,6-hexane diamine showing the best performance. The supported catalysts are more effective than their soluble counterparts. Key chemicals involved in the research include various chiral triamines synthesized from 1,2- or 1,6-diamines and natural α-amino acids like L-valine, 3,5-bis(trifluoromethyl) phenyl isocyanate or isotiocyanate for the formation of ureas and thioureas, and nitroalkanes such as nitromethane as reactants in the aza-Henry reaction. The study also involves the use of different N-Boc aldimines with various substituents on the aryl group to test the generality of the reaction. The supported catalysts demonstrated good recyclability, maintaining enantioselection and showing only slight decreases in activity over multiple cycles.
The study investigates the synthesis and structural properties of stable peptide helices incorporating CR-tetrasubstituted R-amino acids, specifically focusing on the unnatural amino acid rac-14. The researchers synthesized 13 different peptides with lengths up to eight residues, using alternating sequences of rac-14 and (S)- or (R)-valine. The peptides were characterized by X-ray diffraction, NMR, and CD measurements. The results showed that peptides with an all-S backbone configuration formed right-handed 310-helices, while those with an all-R configuration formed left-handed 310-helices in both solid state and solution. The study demonstrates the potential of these peptides as scaffolds and peptidomimetics due to their stable and predictable secondary structures.
The research aims to develop an efficient chemoenzymatic synthesis of enantiopure 4-amino-2-hydroxy acids, which are valuable as ?-turn mimics for studying the secondary structure of peptides. The study employs a single-pot process in an aqueous medium, using carbobenzyloxy (CBZ)-protected 4-amino-2-keto esters derived from L-amino acids (alanine, leucine, phenylalanine, and valine) as substrates. Lipase from Candida rugosa is used to hydrolyze the keto esters to keto acids. The study compares the performance of wild-type lactate dehydrogenases (LDHs) from Bacillus stearothermophilus (BS-LDH) and Staphylococcus epidermidis (SE-LDH) with the genetically engineered H205Q mutant of D-hydroxyisocaproate dehydrogenase (LB-hicDH) in reducing the keto acids to the corresponding 2-hydroxy acids. The wild-type LDHs effectively reduced the alanine-derived keto acid but were inefficient with more bulky substrates. In contrast, the H205Q mutant demonstrated broad substrate specificity and high catalytic activity, successfully reducing all tested keto acids to yield the desired 4-amino-2-hydroxy acids as single diastereomers with excellent yields. The study concludes that the H205Q mutant has significant potential for the large-scale production of these compounds due to its enhanced performance and versatility.
This research investigates the development and evaluation of N-substituted peptides containing α,α-difluorostatone residues as potent inhibitors of human leukocyte elastase (HLE), a serine protease implicated in various diseases such as emphysema and arthritis. The study aims to design inhibitors that can effectively bind to HLE and inhibit its activity, potentially serving as therapeutic agents. Key chemicals used include α,α-difluorostatone derivatives of amino acids like L-valine, L-leucine, and L-phenylalanine, with the α,α-difluoromethylene ketone derivative of L-valine proving to be the most effective at the P1 position. The peptides also incorporate a nonproteinogenic residue, N-(2,3-dihydro-lH-inden-2-yl)glycine, at the P2 position, which acts as a bioisosteric replacement for L-proline. The most potent in vitro compound, 17b, has an IC50 of 0.635 μM. Extended inhibitors like 23b and 24b were designed to interact with additional binding subsites of HLE, enhancing their potency. The study concludes that these α,α-difluoromethylene ketone inhibitors effectively inhibit HLE through transition-state analog mechanisms, forming reversible hemiketals with the active site Ser195 of HLE. The inhibitors were also tested in an elastase-induced pulmonary hemorrhage model in hamsters, with 22c showing significant inhibition of hemorrhage in a dose-dependent manner. The research highlights the potential of these peptides as therapeutic agents for HLE-related diseases.
This research investigates the synthesis, characterization, and hydrogen-bonding interactions of a series of ferrocene (Fc) peptide conjugates containing the amino acid valine. The study aims to understand the role of hydrogen bonding in these compounds, which are relevant to the design of functional peptidic materials and the study of protein folding and aggregation processes. The researchers synthesized Fc-peptide conjugates with various hydrophobic amino acid sequences, including Leu-Val, Val-Phe, Gly-Val, and Val-Phe-Phe, mimicking parts of the amyloid beta-peptide sequence associated with Alzheimer's disease. They used variable temperature 1H NMR spectroscopy, CD spectroscopy, and single crystal X-ray crystallography to study the hydrogen-bonding interactions and structures of these compounds. The results showed that the compounds exhibit intramolecular hydrogen bonding in a "Herrick motif," which stabilizes their structure. In the solid state, the compounds form different supramolecular architectures due to variations in intermolecular hydrogen bonding, with one compound forming head-to-tail stacking interactions and another forming a more open structure with hydrophobic channels.
The study focuses on the synthesis and application of chiral amino thiols as catalysts in the enantioselective addition of diethylzinc to aldehydes, starting from (S)-(-)-valine. A series of new chiral amino thiol and corresponding thioacetate ligands were prepared and utilized in the asymmetric addition, demonstrating excellent enantioselectivity of up to 99% ee with a remarkably low catalyst loading of 0.02mol%. The study highlights the superior performance of these chiral amino thiols compared to traditional amino alcohols, attributing this to the softness of sulfur which exhibits a greater affinity to zinc, in line with the hard soft acid base (HSAB) principle. The research also explores the effect of reaction temperature and solvent on enantioselectivity, finding that less polar solvents without coordinating atoms are more favorable for achieving high ee values. The results underscore the potential of these chiral ligands in asymmetric catalysis, offering a highly efficient and stereoselective method for the addition of diethylzinc to aldehydes.
The research focuses on the synthesis and evaluation of dolastatin 10 analogues, which are of significant interest in cancer research due to their potent in vitro activity and potential use as payloads in antibody drug conjugates (ADCs). The study aims to modify the P2 subunit of the dolastatin 10 core scaffold by introducing heteroatoms to the P2 side chain, resulting in compounds that maintain potent in vitro activity. The most active compounds were found to contain azides in the P2 unit and required a phenylalanine-derived P5 subunit. The researchers synthesized a series of auristatins, which are derivatives of dolastatin 10, using various amino acids and chemical modifications, including amines, azides, oxygens, and thiols. Key chemicals used in the synthesis process included Fmoc-protected amino acids, CMPI (2-chloro-1-methylpyridinium iodide), HATU (1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate), TFA (trifluoroacetic acid), and other reagents for specific coupling and deprotection steps. The conclusions of the research indicated that the P2 side chain modifications could be active in vitro, but these modified compounds followed a different activity trend than valine-based P2 compounds, and the presence of an ester or amide at the P5 position was crucial for the activity of these molecules in vitro.
This research presents the synthesis and evaluation of novel prodrugs of naproxen, a nonsteroidal anti-inflammatory drug (NSAID), aimed at enhancing its pharmaceutical and pharmacokinetic properties while reducing gastrointestinal (GI) toxicity. The study involved the reaction of naproxen with thionyl chloride to form an acid chloride, which was then reacted with glucose to produce glucosyl naproxen. This was followed by acetylation and reaction with various amino acids to yield the prodrugs. The synthesized prodrugs were evaluated for analgesic and anti-inflammatory activities and assessed for GI toxicity. The results indicated that the prodrugs maintained the therapeutic activities of naproxen while significantly reducing GI irritation. Key chemicals used in the synthesis process included naproxen, thionyl chloride, glucose, pyridine, acetic anhydride, and different amino acids such as glycine, valine, alanine, cysteine, and others. The synthesized compounds were characterized using IR, NMR, and MS spectral methods. The study concluded that these novel prodrugs could be potentially useful naproxen derivatives for oral administration due to their stability in aqueous solutions, retention of analgesic and anti-inflammatory activity, and notably reduced GI irritation.
The research explores the application of the Sonogashira reaction to couple alkenyl chlorides with aliphatic acetylenes, aiming to develop a method for synthesizing enediynes from amino acid derivatives. This approach is significant as it offers an alternative to the more expensive and unstable vinyliodides commonly used in natural product synthesis. The study found that using piperidine as a base and optimizing reaction conditions were crucial for successful coupling, especially with less reactive alkenyl chlorides. The researchers synthesized various enediyne-bridged peptide motifs using amino acids like glycine, alanine, valine, phenylalanine, tyrosine, and lysine, achieving yields ranging from 30% to 77%. The results demonstrate the potential of the Sonogashira reaction for synthesizing complex natural products and highlight its applicability in creating enediyne structures with promising biological activities, such as DNA cleavage and antimicrobial properties.
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