162929-44-4Relevant articles and documents
Development of dynamic kinetic resolution on large scale for (±)-1-phenylethylamine
Thalen, Lisa K.,Baeckvall
, p. 823 - 829 (2010)
Candida antarctica lipase B (CALB) and racemization catalyst 4 were combined in the dynamic kinetic resolution (DKR) of (±)-1- phenylethylamine (1). Several reaction parameters have been investigated to modify the method for application on multigram scale
Isopropyl 2-ethoxyacetate—an efficient acylating agent for lipase-catalyzed kinetic resolution of amines in batch and continuous-flow modes
Oláh, Márk,Boros, Zoltán,Hornyánszky, Gábor,Poppe, László
, p. 7249 - 7255 (2016)
Productivity [conversion (c) and specific reaction rate (rbatchor rflow)] and enantiomer selectivity [enantiomeric ratio (E) and enantiomeric excess (ee) of the products] of ethyl and isopropyl esters of acetic, 2-methoxyacetic and 2-ethoxyacetic acids as acylating agents were compared in the N-acylation of (±)-1-phenylethanamine rac-1 catalyzed by variously immobilized forms of Candida antarctica lipase B (CaLB) using shake flasks and continuous-flow reactors. The effect of the temperature in the 0–80 °C range on productivity and enantiomer selectivity in KRs of rac-1 was investigated with the isopropyl esters in continuous-flow mode using CaLB-filled minireactors. Isopropyl 2-ethoxyacetate surpassed the performance of ethyl 2-methoxyacetate in terms of both productivity (1.9–2.9 times higher rate in batch mode) and enantiomeric selectivity (ee(R)-amide>99.9% compared to 99.8%) providing at 40 °C high volumetric productivity (2.22 kg L?1h?1), specific reaction rate and enantiomeric excess (rflow=783 μmol min?1g?1, ee(R)-2c>99.9%).
Positional immobilization of Pd nanoparticles and enzymes in hierarchical yolk-shell@shell nanoreactors for tandem catalysis
Zhang, Xiaoming,Jing, Lingyan,Chang, Fangfang,Chen, Shuai,Yang, Hengquan,Yang, Qihua
, p. 7780 - 7783 (2017)
A hierarchical yolk-shell@shell nanoreactor that spatially positioned Pd nanoparticles and the CALB enzyme in separated domains is constructed, and served as an efficient bifunctional catalyst for the one-pot dynamic kinetic resolution (DKR) reaction of 1
Ammonium formate as a green hydrogen source for clean semi-continuous enzymatic dynamic kinetic resolution of (+/-)-α-methylbenzylamine
De Miranda, Amanda S.,De Souza, Rodrigo O. M. A.,Miranda, Leandro S. M.
, p. 13620 - 13625 (2014)
The chemoenzymatic dynamic kinetic resolution of (+/-)-α- methylbenzylamine under continuous flow conditions in the presence of Pd/BaSO4 as racemization catalyst and ammonium formate as reductant is described. Under the conditions good conversions and excellent enantiomeric excess are reported. This journal is the Partner Organisations 2014.
Modification of supported Pd catalysts by alkalic salts in the selective racemization and dynamic kinetic resolution of primary amines
Jin, Qianru,Jia, Guoqing,Zhang, Yanmei,Li, Can
, p. 464 - 471 (2014)
Supported Pd nanoparticles (PdNPs) were modified with various alkalic salts by incipient wetness impregnation method. The effect of the salts on the catalytic activity and selectivity behavior of Pd catalysts for the racemization of (S)-1-phenylethylamine was investigated. The presence of alkalic salts can greatly enhance the selectivity of Pd catalysts, without significantly decreasing the catalytic activity. This modification method is suitable for PdNPs supported on various supports, such as micro/mesoporous silica and activated carbon. Combined with the immobilized lipases (Novozyme 435), this catalyst system can efficiently catalyze the dynamic kinetic resolution (DKR) of 1-phenylethylamine with yield and enantioselectivity up to 97% and 99%, respectively. The Royal Society of Chemistry.
Optically active amines via lipase-catalyzed methoxyacetylation
Balkenhohl, Friedhelm,Ditrich, Klaus,Hauer, Bernhard,Ladner, Wolfgang
, p. 381 - 384 (1997)
Racemic amines can be efficiently resolved using ethylmethoxyacetate as acylating agent in a lipase-catalyzed reaction. The reaction of 1-phenyethylamine with ethylmethoxyacetate in the presence of a lipase from Burkholderia plantarii is presented. Excellent yields and selectivity and minimal amount of enzyme characterize this new process. Johann Ambrosius Barth 1997.
Fast racemization and dynamic kinetic resolution of primary benzyl amines
Kim, Yunwoong,Park, Jaiwook,Kim, Mahn-Joo
, p. 5581 - 5584 (2010)
We prepared a Pd nanocatalyst (average diameter of Pd nanoparticles = 1.73 nm) displaying a remarkable activity for the racemization and dynamic kinetic resolution (DKR) of 1-methylbenzylamine. It was eight times more active than the previous best. The DKR of 1-methylbenzylamine with the Pd nanocatalyst (2 mol %) in the presence of a thermostable lipase (Novozym 435) was complete in 6 h at 70 °C. The DKRs of other benzyl amines also proceeded to completion in 6 h under similar conditions except the amount of Pd nanocatalyst.
Co-immobilization of an enzyme and a metal into the compartments of mesoporous silica for cooperative tandem catalysis: An artificial metalloenzyme
Engstroem, Karin,Johnston, Eric V.,Verho, Oscar,Gustafson, Karl P. J.,Shakeri, Mozaffar,Tai, Cheuk-Wai,Baeckvall, Jan-E.
, p. 14006 - 14010 (2013)
Surpassing nature: A hybrid catalyst in which Candida antarctica lipase B and a nanopalladium species are co-immobilized into the compartments of mesoporous silica is presented. The metal nanoparticles and the enzyme are in close proximity to one another in the cavities of the support. The catalyst mimics a metalloenzyme and was used for dynamic kinetic resolution of a primary amine in high yield and excellent enantioselectivity. Copyright
Combining Pd nanoparticles on MOFs with cross-linked enzyme aggregates of lipase as powerful chemoenzymatic platform for one-pot dynamic kinetic resolution of amines
Wang, Meng,Wang, Xiaoxu,Feng, Bo,Li, Yuanhua,Han, Xinchen,Lan, Zijie,Gu, Huajun,Sun, Huamin,Shi, Meng,Li, Hexing,Li, Hui
, p. 153 - 163 (2019)
Acquisition of chiral amines is a very important item in scientific research. Chemoenzymatic catalyst combination of Pd nanoparticles supported on the external surface of the ethylenediamine-functionalized MIL-101 (Pd?ED-MIL-101) with layered cross-linked
New Biosilified Pd-lipase hybrid biocatalysts for dynamic resolution of amines
de Souza, Stefania P.,Le?o, Raquel A.C.,Bassut, Jonathan F.,Leal, Ivana C.R.,Wang, Shuai,Ding, Qiqi,Li, Yingying,Lam, Frank Leung-Yuk,de Souza, Rodrigo O.M.A.,Itabaiana Jr, Ivaldo
, p. 4849 - 4854 (2017)
In this work lipase CaLB was immobilized on functionalized Pd-SiO2 nanoparticles in order to simplify the DKR of α-methylbenzylamine. Hybrid biocatalysts showed immobilization efficiencies of 82%, 80% and 76% when containing 1, 5 and 10% of Pd respectively. On DKR reaction values of ee > 99% and conversion of 82% were found with only 1% of Pd, generating a productivity of 2.21 mg of product h?1 mg of support?1 against 0.76 found by N435. Compared to commercial N435, the novel biocatalysts showed protein loads about 15-fold lower and higher activity, demonstrating competitive performances and high industrial applications.
