65609-25-8Relevant academic research and scientific papers
Flow-based enzymatic synthesis of melatonin and other high value tryptamine derivatives: A five-minute intensified process
Contente, Martina Letizia,Farris, Stefano,Tamborini, Lucia,Molinari, Francesco,Paradisi, Francesca
supporting information, p. 3263 - 3266 (2019/06/24)
To increase the uptake of biocatalytic processes by industry, it is essential to demonstrate the reliability of enzyme-based methodologies directly applied to the production of high value products. Here, a unique, efficient, and sustainable enzymatic platform for the multi-gram synthesis of melatonin, projected to generate around 1.5 billion U.S. dollars worldwide by 2021, and its analogues was developed. The system exploits the covalent immobilization of MsAcT (transferase from Mycobacterium smegmatis) onto agarose beads increasing the robustness and longevity of the immobilized biocatalyst. The fully-automated process deriving from the integration between biocatalysis and flow chemistry is designed to maximize the overall yields (58-92%) and reduce reaction times (5 min), overcoming the limitation often associated with bioprocesses and bridging the gap between lab scale and industrial production.
Biocatalytic N-Acylation of Amines in Water Using an Acyltransferase from Mycobacterium smegmatis
Contente, Martina Letizia,Pinto, Andrea,Molinari, Francesco,Paradisi, Francesca
, p. 4814 - 4819 (2018/11/10)
A straightforward one-step biocatalyzed synthesis of different N-acyl amides in water was accomplished using the versatile and chemoselective acyltransferase from Mycobacterium smegmatis (MsAcT). Acetylation of primary arylalkyl amines was achieved with a range of acetyl donors in biphasic systems within 1 hour and at room temperature. Vinyl acetate was the best donor which could be employed in the N-acetylation of a large range of primary amines in excellent yields (85–99%) after just 20 minutes. Other acyl donors (including formyl-, propionyl-, and butyryl-donors) were also efficiently employed in the biocatalytic N-acylation. Finally, the biocatalyst was tested in transamidation reactions using acetamide as acetyl donor in aqueous medium, reaching yields of 60–70%. This work expands the toolbox of preparative methods for the formation of N-acyl amides, describing a biocatalytic approach easy to accomplish under mild conditions in water. (Figure presented.).
Mesyl guaiacol: A versatile intermediate for the synthesis of 5-aminomethyl guaiacol and related compounds
Bensel, Nicolas,Pevere, Virginie,Desmurs, Jean Roger,Wagner, Alain,Mioskowski, Charles
, p. 4281 - 4283 (2007/10/03)
An original synthetic pathway for the preparation of 5-substituted guaiacol derivatives is described. This method relies on the deactivation of the phenol group by converting it into the corresponding mesyl ester. Amidomethylation reactions lead to regioselective C-C bond formation at the 5-position of guaiacol. Thus, 5-aminomethyl-guaiacol was obtained in four steps and 75% overall yield.
Application of the ortho-Lithiation-Cyclization Strategy to N-Benzyl- and N-Phenethylamine Derivatives
Lete, Esther,Collado, M. Isabel,Sotomayor, Nuria,Vicente, Teresa,Villa, Maria-Jesus
, p. 1751 - 1758 (2007/10/03)
The ortho-lithiation-cyclization of iodinated N,N-diacylphenethylamines provides a convenient method for the preparation of 2-(2-acetoamidoethyl)acetophenones and 2-(2-benzamidoethyl)benzophenones, which could be easily transformed into dihydroisoquinolines.By contrast, the N-ethylamino, N-acetylamino, and N-trimethylsilylamino moieties studied as ortho-directing groups provide poor assistance to the metalation of N-benzyl- and N-phenyethylamines and the corresponding isoindolone or isoquinolone derivatives are obtained in low yields.
Direct Synthesis of Benzophenanthridines and Benzophenanthridones via SRN1 Reactions
Beugelmans, Rene,Chastanet, Jacqueline,Ginsburg, Helene,Quintero-Cortes, Leticia,Roussi, Georges
, p. 4933 - 4938 (2007/10/02)
A straightforward and high-yield route to the 11,12-dihydrobenzophenanthridine (3) and 11,12-dihydrobenzophenanthridone (14) ring systems is based upon an SRN1 reaction between 2-halobenzylamines 1 or 2-halobenzoic acids 11 and enolates derived from tetralones 2.The efficient dehydrogenation of 3 or 14 gives the benzophenthridines 4 or benzophenanthridones 15.Use of properly substituted reactants leads to nitidine, avicine, and fagaronine and to analogues of those natural products.
