15397-33-8Relevant articles and documents
Characterization of Carboxylic Acid Reductases as Enzymes in the Toolbox for Synthetic Chemistry
Finnigan, William,Thomas, Adam,Cromar, Holly,Gough, Ben,Snajdrova, Radka,Adams, Joseph P.,Littlechild, Jennifer A.,Harmer, Nicholas J.
, p. 1005 - 1017 (2017/03/27)
Carboxylic acid reductase enzymes (CARs) meet the demand in synthetic chemistry for a green and regiospecific route to aldehydes from their respective carboxylic acids. However, relatively few of these enzymes have been characterized. A sequence alignment with members of the ANL (Acyl-CoA synthetase/ NRPS adenylation domain/Luciferase) superfamily of enzymes shed light on CAR functional dynamics. Four unstudied enzymes were selected by using a phylogenetic analysis of known and hypothetical CARs, and for the first time, a thorough biochemical characterization was performed. Kinetic analysis of these enzymes with various substrates shows that they have a broad but similar substrate specificity. Electron-rich acids are favored, which suggests that the first step in the proposed reaction mechanism, attack by the carboxylate on the α-phosphate of adenosine triphosphate (ATP), is the step that determines the substrate specificity and reaction kinetics. The effects of pH and temperature provide a clear operational window for the use of these CARs, whereas an investigation of product inhibition by NADP+, adenosine monophosphate, and pyrophosphate indicates that the binding of substrates at the adenylation domain is ordered with ATP binding first. This study consolidates CARs as important and exciting enzymes in the toolbox for sustainable chemistry and provides specifications for their use as a biocatalyst.
Synthesis of the naphthalenone, dihydroquinoline, and dihydrofuran derivatives
Guengoer, Fuesun Seyma,Anac, Olcay,Sezer, Oezkan
experimental part, p. 1115 - 1129 (2011/08/05)
The reactions of enaminones with dimethyl diazomalonate were investigated in the presence of copper(II) acetylacetonate. From the reaction of (E)-3-[methyl(phenyl)amino]-1-phenylprop-2-en-1-one (6c), dimethyl 2-[methyl(phenyl)amino]-4-oxonaphthalene-1,1-(4H)-dicarboxylate, was unexpectedly obtained as the major product. Quinoline derivatives were formed as the major products in the case of N-methyl-p-anisidino and N-methyl-p-toluidino enaminones. The reactions of acetyl enaminones were also realized, and quinoline derivatives were isolated as the major products. 3H- and 5H-dihydrofurans were also formed as side products in these reactions. These results differ from those reported earlier on the reactions of tertiary enaminones with carbenes/metal carbenes.
Identification and optimisation of 5-amino-7-aryldihydro-1,4-diazepines as 5-HT2A ligands
Swain, Christopher J.,Teran, Ana,Maroto, Marta,Cabello, Angeles
, p. 6058 - 6062 (2007/10/03)
A several series of low molecular weight 5-HT2A leads were identified from an analysis of HTS data, the exploration of SAR and optimization of one series using parallel synthesis are described, affording compound 22 (5-HT2A IC50 1.1 nM).
