3197-42-0Relevant articles and documents
A Novel (R)-Imine Reductase from Paenibacillus lactis for Asymmetric Reduction of 3 H-Indoles
Li, Hao,Zhang, Guang-Xiang,Li, Liu-Mei,Ou, Yu-Shi,Wang, Ming-Yang,Li, Chun-Xiu,Zheng, Gao-Wei,Xu, Jian-He
, p. 724 - 727 (2016)
A novel (R)-imine reductase (PlRIR) from Paenibacillus lactis was heterologously overexpressed in Escherichia coli, purified and characterized. The purified PlRIR exhibited relatively high catalytic efficiency (kcat/Km=1.58 s-1 mm-1) towards 2,3,3-trimethylindolenine. A panel of 3H-indoles and 3H-indole iodides were reduced by PlRIR to yield the corresponding products with good-to-excellent enantioselectivity (66-98 % ee). In addition, PlRIR also possesses good activities toward other types of imines such as pyrroline, tetrahydropyridine, and dihydroisoquinoline, indicating a reasonably broad substrate acceptance. In a 100 mg scale preparative reaction, 100 mm 2,3,3-trimethylindolenine was converted efficiently to afford (R)-2,3,3-trimethylindoline with 96 % ee and 81 % yield.
Synthesis of: N -heterocycles from diamines via H2-driven NADPH recycling in the presence of O2
Al-Shameri, Ammar,Borlinghaus, Niels,Weinmann, Leonie,Scheller, Philipp N.,Nestl, Bettina M.,Lauterbach, Lars
, p. 1396 - 1400 (2019/03/26)
Herein, we report an enzymatic cascade involving an oxidase, an imine reductase and a hydrogenase for the H2-driven synthesis of N-heterocycles. Variants of putrescine oxidase from Rhodococcus erythropolis with improved activity were identified. Substituted pyrrolidines and piperidines were obtained with up to 97% product formation in a one-pot reaction directly from the corresponding diamine substrates. The formation of up to 93% ee gave insights into the specificity and selectivity of the putrescine oxidase.
Identification of an Imine Reductase for Asymmetric Reduction of Bulky Dihydroisoquinolines
Li, Hao,Tian, Ping,Xu, Jian-He,Zheng, Gao-Wei
supporting information, p. 3151 - 3154 (2017/06/23)
A new imine reductase from Stackebrandtia nassauensis (SnIR) was identified, which displayed over 25- to 1400-fold greater catalytic efficiency for 1-methyl-3,4-dihydroisoquinoline (1-Me DHIQ) compared to other imine reductases reported. Subsequently, an efficient SnIR-catalyzed process was developed by simply optimizing the amount of cosolvent, and up to 15 g L-1 1-Me DHIQ was converted completely without a feeding strategy. Furthermore, the reaction proceeded well for a panel of dihydroisoquinolines, affording the corresponding tetrahydroisoquinolines (mostly in S-configuration) in good yields (up to 81%) and with moderate to excellent enantioselectivities (up to 99% ee).