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
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
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.
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.
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
Synthesis and characterization of a magnetic hybrid catalyst containing lipase and palladium and its application on the dynamic kinetic resolution of amines
Almeida, Rhudson F. O.,Caraballo, Richard,Dalm?nico, Gisele,Ferraz, Clara A.,Finotelli, Priscilla V.,Itabaiana, Ivaldo,Junior, Aldo A. T.,Le?o, Raquel A. C.,Sergio, Gabriella G.,Wojcieszak, Robert,de Souza, Rodrigo O. M. A.,do Nascimento, Marcelo A.
, (2020)
Recent papers estimates that about 40 % of drugs present chiral amines in their structure and their synthesis in a sustainable and cost-competitive way is still a challenge for the industry. Kinetic resolution is one of the most applied method to produce these desired compounds where the association with lipase as a catalyst is a good alternative. However, the use of separate racemization catalyst and enzymes in the reaction medium still limits recovery, recycling and can occasionally be responsible for decreasing in selectivity for the desired product. In this work we proposed the synthesis and characterization of a hybrid magnetic catalyst composed containing lipase CaL B and Pd immobilized on the same recovered nanometric magnetic support for the application on Dynamic Kinetic Resolution of (rac)-1-phenylethylamine both in batch and continuous flow conditions. As results it was possible to achieve 99 % of conversion, with 95 % of selectivity and 93 % of enantiomeric excess after 12 h in batch. For a continuous flow system, it was possible to achieve 95 % of conversion with 71 % of selectivity and ee > 99 % after 60 min of reaction. The hybrid catalyst had around 50?100 nm with nanoparticulated Pd (5?10 nm) on its surface, presented a superparamagnetic behavior without remaining magnetization and 22 emu/g of saturation magnetization.
Mesoporous Core-Shell Nanostructures Bridging Metal and Biocatalyst for Highly Efficient Cascade Reactions
Gao, Jing,Gao, Shiqi,Jiang, Yanjun,Liu, Yunting,Ma, Li,Wang, Zihan
, p. 1375 - 1380 (2020/02/06)
Mesoporous core-shell structured nanocatalysts with a PdPt bimetallic core and enzyme-immobilized polydopamine (PDA) shell were designed, in which the PDA shell worked as a barrier to position the bimetallic core and enzyme in separated locations. The accessible mesoporous structures of both the core and shell significantly facilitate mass transfer and catalyst utilization, improving the synergistic catalytic abilities in cascade reactions. The obtained bifunctional nanocatalysts enabled efficient two-step one-pot cascade reactions of different types: dynamic kinetic resolution of primary amines in organic solvent with high yield and enantioselectivity (up to 99% yield and 98% ee) and degradation of organophosphate nerve agent in aqueous solution with high rate constant and turnover frequency number values (0.8 min-1 and 20 min-1, respectively).
Chemoenzymatic Dynamic Kinetic Resolution of Primary Benzylic Amines using Pd0-CalB CLEA as a Biohybrid Catalyst
Gustafson, Karl P. J.,G?rbe, Tamás,de Gonzalo-Calvo, Gonzalo,Yuan, Ning,Schreiber, Cynthia L.,Shchukarev, Andrey,Tai, Cheuk-Wai,Persson, Ingmar,Zou, Xiaodong,B?ckvall, Jan-E.
, p. 9174 - 9179 (2019/07/04)
Herein, we report on the use a biohybrid catalyst consisting of palladium nanoparticles immobilized on cross-linked enzyme aggregates of lipase B of Candida antarctica (CalB CLEA) for the dynamic kinetic resolution (DKR) of benzylic amines. A set of amines were demonstrated to undergo an efficient DKR and the recyclability of the catalysts was studied. Extensive efforts to further elucidate the structure of the catalyst are presented.
