Synonyms:2-ammonio-3-hydroxypropanoate;2-azaniumyl-3-hydroxypropanoate;serine zwitterion;(L) or (D)-serine;CHEBI:35243
98.0% *data from raw suppliers
DL-Serine 99+% *data from reagent suppliers
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There total 94 articles about 2-Ammonio-3-hydroxypropanoate 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: 3.0%
Reference yield: 1.5%
Reference yield: 0.6%
The research investigates the interaction between the macrobicyclic ligand cryptand 222 and various amino acids in methanol. The study aims to provide the first thermodynamic data on the formation of 1:1 complexes between cryptand 222 and amino acids, including glycine, DL-alanine, DL-phenylalanine, DL-serine, DL-proline, and DL-tryptophan, at 298.15 K. Using titration calorimetry and potentiometric titration, the researchers determined the stability constants (log Ks), Gibbs free energy (ΔG°), enthalpy (ΔH°), and entropy (ΔS°) of these complexation reactions. The results indicate that the amino group of the amino acids is the primary active site for interaction with cryptand 222, and the stability of the complexes is influenced by steric factors from substituent groups on the α-carbon of the amino acids. The study concludes that complexation is enthalpically and entropically favored for most amino acids, except glycine. Additionally, computer modeling suggests that the interaction occurs through hydrogen bonds and electrostatic interactions between the amino group and the oxygen atoms of cryptand 222. The findings have implications for understanding the transport of amino acids across cell membranes, enhancing their solubility in organic solvents, and developing methods for their separation.
The study focuses on an improved synthesis of d,l-serine from acrylsulfonic acid ethyl ester. The researchers aimed to develop a more efficient and cost-effective method for synthesizing d,l-serine, building on the work of du Vigneaud and Wood. The process involves several key steps: Initially, a,?-dibromopropionic acid ethyl ester (I) is synthesized by reacting acrylsulfonic acid ethyl ester with bromine. This compound (I) is then converted to a-bromo-?-ethoxypropionic acid ethyl ester (II) using sodium ethylate in the presence of catalytic amounts of mercury(II) acetate in absolute alcohol. The presence of mercury(II) salts and the water content of the medium are identified as crucial factors in directing the reaction towards the desired product. The bromine in compound (II) is subsequently replaced by an azide group to form a-azido-?-ethoxypropionic acid ethyl ester (III), which is then reduced to a-amino-?-ethoxypropionic acid ethyl ester hydrochloride (IV) using catalytic hydrogenation. Finally, the ethyl ester (IV) is hydrolyzed to yield d,l-serine hydrobromide (V), which is purified to obtain d,l-serine (VI). The study highlights the importance of reaction conditions and catalysts in achieving high yields and purity of the final product, with an overall yield of 61% for the synthesis of d,l-serine from the starting material.
The research focuses on the kinetics of the arenesulfonylation reaction involving DL-serine, L-proline, DL-threonine, and DL-methionine with 3-nitrobenzenesulfonyl chloride (3-NBSC) in mixed solvent systems of 1,4-dioxane—water and propan-2-ol—water. The study was conducted spectrophotometrically at 298 K to determine the reaction rate constants and understand the reactive forms of the amino acids. The main reactive form was found to be anionic, and the basicity of the α-amino acids was identified as a crucial factor in determining the reaction rate. The rate constants for arenesulfonylation were compared with those of N-acylation with benzoyl chloride and reactions with benzoic acid 4-nitrophenyl ester. The experiments involved monitoring the reaction's progress by tracking changes in 3-NBBSC concentration at 242 nm using a spectrophotometer. The reaction conditions, including pH, were controlled using an acetate buffer, and the pH was measured with an ionomer. The research aimed to optimize synthetic conditions for sulfamides, which are important due to their role in enzyme inhibition and as protective groups in organic synthesis.
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