177750-54-8Relevant articles and documents
Generation of amine dehydrogenases with increased catalytic performance and substrate scope from ε-deaminating L-Lysine dehydrogenase
Tseliou, Vasilis,Knaus, Tanja,Masman, Marcelo F.,Corrado, Maria L.,Mutti, Francesco G.
, (2019)
Amine dehydrogenases (AmDHs) catalyse the conversion of ketones into enantiomerically pure amines at the sole expense of ammonia and hydride source. Guided by structural information from computational models, we create AmDHs that can convert pharmaceutically relevant aromatic ketones with conversions up to quantitative and perfect chemical and optical purities. These AmDHs are created from an unconventional enzyme scaffold that apparently does not operate any asymmetric transformation in its natural reaction. Additionally, the best variant (LE-AmDH-v1) displays a unique substrate-dependent switch of enantioselectivity, affording S- or R-configured amine products with up to >99.9% enantiomeric excess. These findings are explained by in silico studies. LE-AmDH-v1 is highly thermostable (Tm of 69 °C), retains almost entirely its catalytic activity upon incubation up to 50 °C for several days, and operates preferentially at 50 °C and pH 9.0. This study also demonstrates that product inhibition can be a critical factor in AmDH-catalysed reductive amination.
A highly effective rhodium spirocyclic phosphinite catalyst for the asymmetric hydrogenation of enamides
Hu, Wenhao,Yan, Ming,Lau, Chak-Po,Yang,Chan, Albert S.C.A.,Jiang, Yaozhong,Mi, Aiqiao
, p. 973 - 976 (1999)
A rhodium complex of the phosphinite ligand spirOP was found to be an effective catalyst for the asymmetric catalytic hydrogenation of α- substituted enamides with ee values ranging from 85.1% to 97.4%.
Metallacrown ether catalysts containing phosphine-phosphite polyether ligands for Rh-catalyzed asymmetric hydrogenation - Enhancements in activity and enantioselectivity
Song, Feng-Tao,Ouyang, Guang-Hui,Li, Yong,He, Yan-Mei,Fan, Qing-Hua
, p. 6713 - 6719 (2014)
A new class of tunable metallacrown ether rhodium catalysts based on α,ω-(phosphine-phosphite) polyether ligands were prepared either by a template-induced method or by a nontemplate procedure. For the asymmetric hydrogenation of α-arylenamides with the a
Biocatalytic, Intermolecular C?H Bond Functionalization for the Synthesis of Enantioenriched Amides
Arnold, Frances H.,Athavale, Soumitra V.,Gao, Shilong,Hirschi, Jennifer S.,Liu, Zhen,Mallojjala, Sharath Chandra
supporting information, p. 24864 - 24869 (2021/10/15)
Directed evolution of heme proteins has opened access to new-to-nature enzymatic activity that can be harnessed to tackle synthetic challenges. Among these, reactions resulting from active site iron-nitrenoid intermediates present a powerful strategy to forge C?N bonds with high site- and stereoselectivity. Here we report a biocatalytic, intermolecular benzylic C?H amidation reaction operating at mild and scalable conditions. With hydroxamate esters as nitrene precursors, feedstock aromatic compounds can be converted to chiral amides with excellent enantioselectivity (up to >99 % ee) and high yields (up to 87 %). Kinetic and computational analysis of the enzymatic reaction reveals rate-determining nitrenoid formation followed by stepwise hydrogen atom transfer-mediated C?H functionalization.
Development of robust heterogeneous chiral rhodium catalysts utilizing acid?base and electrostatic interactions for efficient continuous-flow asymmetric hydrogenations
Saito, Yuki,Kobayashi, Shu
supporting information, p. 16546 - 16551 (2020/11/09)
Heterogeneous chiral Rh catalysts based on acid?base and electrostatic interactions have been developed. The robust catalysts demonstrate high activity and selectivity in the continuous-flow asymmetric hydrogenation of a wide variety of enamides and dehyd
