title: Efficient asymmetric synthesis of 1-cyano-tetrahydroisoquinolines from lipase dual activity and opposite enantioselectivities in α-Aminonitrile resolution.
abstract: Dual promiscuous racemization/amidation activities of lipases leading to efficient dynamic kinetic resolution protocols of racemic α-aminonitrile compounds are described. α-Amidonitrile products of high enantiomeric purity could be formed in high yields. Several lipases from different sources were shown to exhibit the dual catalytic activities, where opposite enantioselectivities could be recorded for certain substrates.
authors: KTH Royal Institute of Technology Department of Chemistry, Teknikringen 30, 10044 Stockholm (Sweden).
authors: Morakot
authors: M
authors: Sakulsombat
authors: Pornrapee
authors: P
authors: Vongvilai
authors: Olof
authors: O
authors: Ramström
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D000586:Amination; D019117:Burkholderia / Q000201:enzymology*; D002175:Candida / Q000201:enzymology*; D007700:Kinetics; D008049:Lipase / Q000378:metabolism*; D009570:Nitriles / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D011549:Pseudomonas / Q000201:enzymology*; D013237:Stereoisomerism; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism
chemical_list: D000577:Amides; D009570:Nitriles; D044005:Tetrahydroisoquinolines; D008049:Lipase
keywords: amidation; asymmetric synthesis; dynamic chemistry; enzymes; lipases; racemization