1021048-45-2Relevant academic research and scientific papers
Amine Transaminase from Exophiala Xenobiotica - Crystal Structure and Engineering of a Fold IV Transaminase that Naturally Converts Biaryl Ketones
Telzerow, Aline,Paris, Juraj,H?kansson, Maria,González-Sabín, Javier,Ríos-Lombardía, Nicolás,Schürmann, Martin,Gr?ger, Harald,Morís, Francisco,Kourist, Robert,Schwab, Helmut,Steiner, Kerstin
, p. 1140 - 1148 (2019)
Amine transaminases are frequently used for the production of chiral amines starting from prochiral ketones. These amines can be applied as active pharmaceutical ingredients or drug precursors. However, there are still limitations to the use of amine transaminases when it comes to bulky ketone substrates, such as biaryl ketones. Using data mining, an (R)-selective amine transaminase from Exophiala xenobiotica was identified which naturally converts biaryl ketone substrates to the corresponding amines with up to 85% conversion and excellent enantioselectivity (>99% ee). Its protein crystal structure was obtained with a resolution of 1.52 ?, which enabled us to explain this interesting substrate acceptance. Structure-guided protein engineering resulted in a quintuple variant with increased stability. Moreover, the amino acid exchange T273S increased the activity and broadened the substrate scope, enabling conversions of various biaryl ketones with up to >99%. A preparative biotransformation of 1-(4-(pyridin-3-yl)phenyl)ethenone at 75 mM (15 g/L) resulted in 96% of isolated yield of the respective amine.
Enantioselective addition of diethylzinc to N-diphenylphosphinoylimines employing N,N-dialkyl-1,2-diphenyl-2-aminoethanols as chiral ligands
Zhang, Xiaomei,Gong, Liuzhu,Mi, Aiqiao,Cui, Xin,Jiang, Yaozhong,C. K. Choi, Michael,S. C. Chan, Albert
, p. 6369 - 6372 (2007/10/03)
By fine-tuning the substituents on the nitrogen of (1S,2R) and (1R,2S)-1,2-diphenyl-2-aminoethanols, a chiral ligand 2b was obtained, which showed excellent enantioselectivity, with up to 94% e.e, for the asymmetric addition of diethylzinc to N-diphenylphosphinoylimines 1. In one example, the optically active amide 3c was converted into a new amine 5 with 98% e.e. by a reaction sequence involving Suzuki coupling and hydrolysis without racemization.
