Chemoenzymatic Synthesis of Optically Active Alcohols Possessing 1,2,3,4-Tetrahydroquinoline Moiety Employing Lipases or Variants of the Acyltransferase from Mycobacterium smegmatis

The enzymatic kinetic resolution (EKR) of racemic alcohols or esters is a broadly recognized methodology for the preparation these compounds in optically active form. Although EKR approaches have been developed enantioselective transesterification vast number secondary hydrolysis their respective esters, to date, there no report bio- chemo-catalytic asymmetric synthesis non-racemic possessing 1,2,3,4-tetrahydroquinoline moiety, which are valuable building blocks pharmaceutical industry. In this work, set 1,2,3,4-tetrahydroquinoline-propan-2-ols was successfully carried out neat organic solvents (in case CAL-B and BCL) water MsAcT single variants) using immobilized lipases from Candida antarctica type B (CAL-B) Burkholderia cepacia (BCL) engineered acyltransferase variants Mycobacterium smegmatis (MsAcT) as biocatalysts vinyl acetate irreversible acyl donor, yielding enantiomerically enriched (S)-alcohols corresponding (R)-acetates with E-values up 328 excellent optical purities (>99% ee). general, higher ee-values were observed reactions catalyzed by lipases; however, rates significantly better MsAcT-catalyzed transesterifications. Interestingly, we experimentally proved that 1-(7-nitro-3,4-dihydroquinolin-1(2H)-yl)propan-2-ol undergoes spontaneous amplification purity under achiral chromatographic conditions.