26184-62-3Relevant articles and documents
Caffeic acid esters and lignans from piper sanguineispicum
Cabanillas, Billy Joel,Le Lamer, Anne-Cecile,Castillo, Denis,Arevalo, Jorge,Rojas, Rosario,Odonne, Guillaume,Bourdy, Genevieve,Moukarzel, Beatrice,Sauvain, Michel,Fabre, Nicolas
, p. 1884 - 1890 (2010)
Three new caffeic acid esters (1-3), four new lignans (4-7), and the known compounds (7′S)-parabenzlactone (8), dihydrocubebin (9), and justiflorinol (10) have been isolated from leaves of Piper sanguineispicum. Their structures were determined by spectroscopic methods, including 1D and 2D NMR, HRCIMS, CD experiments, and chemical methods. Compounds 1-10 were assessed for their antileishmanial potential against axenic amastigote forms of Leishmania amazonensis. Caffeic acid esters 1 and 3 exhibited the best antileishmanial activity (IC50 2.0 and 1.8 μM, respectively) with moderate cytotoxicity on murine macrophages.
Facile Stereoselective Reduction of Prochiral Ketones by using an F420-dependent Alcohol Dehydrogenase
Martin, Caterina,Tjallinks, Gwen,Trajkovic, Milos,Fraaije, Marco W.
, p. 156 - 159 (2020/10/26)
Effective procedures for the synthesis of optically pure alcohols are highly valuable. A commonly employed method involves the biocatalytic reduction of prochiral ketones. This is typically achieved by using nicotinamide cofactor-dependent reductases. In this work, we demonstrate that a rather unexplored class of enzymes can also be used for this. We used an F420-dependent alcohol dehydrogenase (ADF) from Methanoculleus thermophilicus that was found to reduce various ketones to enantiopure alcohols. The respective (S) alcohols were obtained in excellent enantiopurity (>99 % ee). Furthermore, we discovered that the deazaflavoenzyme can be used as a self-sufficient system by merely using a sacrificial cosubstrate (isopropanol) and a catalytic amount of cofactor F420 or the unnatural cofactor FOP to achieve full conversion. This study reveals that deazaflavoenzymes complement the biocatalytic toolbox for enantioselective ketone reductions.
Production of chiral alcohols from racemic mixtures by integrated heterogeneous chemoenzymatic catalysis in fixed bed continuous operation
Carceller, Jose Miguel,Climent, Maria J.,Corma, Avelino,Iborra, Sara,Mifsud, Maria
, p. 2767 - 2777 (2020/06/17)
Valuable chiral alcohols have been obtained from racemic mixtures with an integrated heterogeneous chemoenzymatic catalyst in a two consecutive fixed catalytic bed continuous reactor system. In the first bed the racemic mixture of alcohols is oxidized to the prochiral ketone with a Zr-Beta zeolite and using acetone as the hydrogen acceptor. In the second catalytic bed the prochiral ketone is stereoselectively reduced with an alcohol dehydrogenase (ADH) immobilized on a two dimensional (2D) zeolite. In this process, the alcohol (isopropanol) formed by the reduction of acetone in the first step reduces the cofactor in the second step, and the full reaction cycle is in this way internally closed with 100% atom economy. A conversion of about 95% with ～100% selectivity to either the (R) or the (S) alcohol has been obtained for a variety of racemic mixtures of alcohols.
