1558-58-3Relevant articles and documents
Kunz et al.
, p. 1139,1143-1144 (1978)
Efficient production of enantiomerically pure chiral amines at concentrations of 50 g/L using transaminases
Truppo, Matthew D.,David Rozzell,Turner, Nicholas J.
, p. 234 - 237 (2010)
Two methods for the efficient (50 g/L) production of optically pure amines from their corresponding ketones using transaminases have been developed. The first method utilizes an ion-exchange resin for in situ product removal allowing the reaction to be carried out a substrate concentration of 50 g/L. The second approach relies upon conversion of the initially formed amine, via spontaneous cyclisation, to a noninhibitory product. Both methods have been demonstrated at 50 mL scale. (R)- and (S)-methylbenzylamine, and (R)- and (S)-6-methyl-2- piperidone have been produced in >90% isolated yield and >99% ee.
Conversion of γ- and δ-Keto Esters into Optically Active Lactams. Transaminases in Cascade Processes
Mourelle-Insua, ángela,Zampieri, Luiz Arthur,Lavandera, Iván,Gotor-Fernández, Vicente
supporting information, p. 686 - 695 (2018/02/21)
A one-pot two-step enzymatic strategy has been designed for the production of optically active γ- and δ-lactams in aqueous medium under mild conditions. The approach is based on the biotransamination of ethyl or methyl keto esters bearing different alkyl or aryl substitution patterns at α-position to the ketone functionality. In this manner, the keto esters were transformed into the corresponding amino esters with excellent conversions, which underwent spontaneous cyclisation in the reaction medium without addition of external reagents. Depending on the transaminase selectivity, both lactam enantiomers can be obtained, so initial enzyme screenings were performed using commercially available and made in house enzymes. Reaction conditions were optimised focusing on the substrate concentration, temperature and ratio of amine donor vs acceptor. Thus, ten γ- and δ-lactams were obtained in good to high isolated yields (70–90%) and excellent selectivities (94–99%) after one or two days at 30 or 45 °C. (Figure presented.).
