54229-53-7Relevant academic research and scientific papers
Biocatalytic Asymmetric Synthesis of N-Aryl-Functionalized Amino Acids and Substituted Pyrazolidinones
Fu, Haigen,Prats Luján, Alejandro,Bothof, Laura,Zhang, Jielin,Tepper, Pieter G.,Poelarends, Gerrit J.
, p. 7292 - 7299 (2019/08/26)
N-arylated α-amino acids and pyrazolidin-3-ones are widely being used as chiral building blocks for pharmaceuticals and agrochemicals. Here we report a biocatalytic route for the asymmetric synthesis of various N-arylated aspartic acids applying ethylenediamine-N,N′-disuccinic acid lyase (EDDS lyase) as a biocatalyst. This enzyme shows a broad substrate scope, enabling the addition of a variety of arylamines to fumarate with high conversions, yielding the corresponding N-arylated aspartic acids in good isolated yields and with high enantiomeric excess (ee > 99%). Furthermore, we developed a chemoenzymatic method toward the synthetically challenging chiral 2-aryl-5-carboxylpyrazolidin-3-ones, using arylhydrazines as bis-nucleophilic donors in the EDDS lyase catalyzed hydroamination of fumarate followed by an acid-catalyzed intramolecular amidation, achieving good overall yields and high optical purity (ee > 99%). In addition, we successfully combined the EDDS lyase catalyzed hydroamination and acid-catalyzed cyclization steps in one pot, thus providing a simple chemoenzymatic cascade route for synthesis of enantiomerically pure pyrazolidin-3-ones. Hence, these biocatalytic methods provide convenient alternative routes to important chiral N-arylated aspartic acids and difficult 2-aryl-5-carboxylpyrazolidin-3-ones.
The conversion of a phenol to an aniline occurs in the biochemical formation of the 1-(4-aminophenyl)-1-deoxy- d -ribitol moiety in methanopterin
White, Robert H.
experimental part, p. 6041 - 6052 (2012/06/04)
Recent work has demonstrated that 4-hydroxybenzoic acid is the in vivo precursor to the 1-(4-aminophenyl)-1-deoxy-d-ribitol (APDR) moiety present in the C1 carrier coenzyme methanopterin present in the methanogenic archaea. For this transformation to occur, the hydroxyl group of the 4-hydroxybenzoic acid must be replaced with an amino group at some point in the biosynthetic pathway. Using stable isotopically labeled precursors and liquid chromatography with electrospray-ionization mass spectroscopy, the first step of this transformation in Methanocaldococcus jannaschii occurs by the reaction of 4-hydroxybenzoic acid with phosphoribosyl pyrophosphate (PRPP) to form 4-(β-d-ribofuranosyl)hydroxybenzene 5′-phosphate (β-RAH-P). The β-RAH-P then condenses with l-aspartate in the presence of ATP to form 4-(β-d-ribofuranosyl)-N-succinylaminobenzene 5′-phosphate (β-RFSA-P). Elimination of fumarate from β-RFSA-P produces 4-(β-d-ribofuranosyl)aminobenzene 5′-phosphate (β-RFA-P), the known precursor to the APDR moiety of methanopterin [White, R. H. (1996) Biochemistry 35, 3447-3456]. This work represents the first biochemical example of the conversion of a phenol to an aniline.
Use of diphenyliodonium bromide in the synthesis of some N-phenyl-amino acids
McKerrow, Jason D.,Al-Rawi, Jasim M. A.,Brooks, Peter
experimental part, p. 1161 - 1179 (2010/04/28)
The N-phenyl methyl esters 4 of glycine, alanine, valine, leucine, isoleucine, phenylalanine, methionine, proline, serine, threonine, tyrosine, aspartic acid, and glutamic acid have been synthesized in good to excellent yields using diphenyliodonium bromide, AgNO3, and a catalytic amount of CuBr starting from the relevant amino acid ester. The chiral integrity of the amino acids 5 was maintained during these reactions, which were confirmed by the synthesis of dipeptide for each N-phenyl amino acid. The structures of the new compounds were confirmed by the analysis of their IR, 1H, and 13C NMR spectra in addition to CHN microanalysis or high-resolution mass spectrometry for the new N-phenyl amino acids 5 and the esters 4.
Synthesis of SB-214857 using copper catalysed amination of arylbromides with L-aspartic acid
Clement,Hayes,Sheldrake,Sheldrake,Wells
, p. 1423 - 1427 (2007/10/03)
An efficient synthesis of a 1,4-benzodiazepine was accomplished using copper catalysed amination of an arylbromide with the soluble bis-tetrabutylammonium salt of L-aspartic acid as a key step.
2-Carboxytetrahydroquinolines. Conformational and Stereochemical Requirements for Antagonism of the Glycine Site on the NMDA Receptor
Carling, Robert W.,Leeson, Paul D.,Moseley, Angela M.,Baker, Raymond,Foster, Alan C.,et al.
, p. 1942 - 1953 (2007/10/02)
2-Carboxy-1,2,3,4-tetrahydroquinoline derivatives, derived from kynurenic acid, have been synthesized and evaluated for in vitro antagonist activity at the glycine site on the NMDA receptor. 2,3-Dihydrokynurenic acids show reduced potency relative to the
1-ARYL-5-CARBOXYMETHYLHYDANTOIN DERIVATIVES. STRUCTURE OF 1-PHENYL-2-THIO-5-CARBOMETHOXYMETHYLHYDANTOIN
Baltrushis, R. S.,Beresnevichyus, Z.-I. G.,Vizgaitis, I. M.,Gatilov, Yu. V.
, p. 1226 - 1231 (2007/10/02)
The reaction of aromatic amines with maleic acid or its diethyl ester with subsequent hydrolysis gave N-arylaspartic acids, which were converted to 1-aryl- and 1-aryl-2-thio-5-carboxymethylhydantoins by the action of urea, cyanates, or thiocyanates in an
