ABSTRACT
This study presents an innovative method for synthesizing ß-amino carbonylated compounds, specifically 2-[phenyl(phenylamino)methyl] cyclohexanone, achieving high conversions and diastereomeric ratios. Using trypsin or α-chymotrypsin in both free and immobilized forms on titanate nanotubes (NtsTi), synthesized through alkaline hydrothermal methods, successful immobilization yields were attained. Notably, α-chymotrypsin, when free, displayed a diastereoselective synthesis of the anti-isomer with 97 % conversion and 16 : 84 (syn : anti) diastereomeric ratio, which slightly decreased upon immobilization on NtsTi. Trypsin, in its free form, exhibited diastereoselective recognition of the syn-isomer, while immobilization on NtsTi (trypsin/NtsTi) led to an inversion of diastereomeric ratio. Both trypsin/NtsTi and α-chymotrypsin/NtsTi demonstrated significant catalytic efficiency over five cycles. In conclusion, NtsTi serves as an effective support for trypsin and α-chymotrypsin immobilization, presenting promising prospects for diastereoselective synthesis and potential industrial applications. Furthermore, it offers promising prospects for the diastereoselective synthesis of 2-[phenyl(phenylamino)methyl] cyclohexanone through multicomponent Mannich reaction and future industrial application.
Subject(s)
Chymotrypsin , Enzymes, Immobilized , Nanotubes , Titanium , Trypsin , Titanium/chemistry , Enzymes, Immobilized/chemistry , Enzymes, Immobilized/metabolism , Chymotrypsin/chemistry , Chymotrypsin/metabolism , Trypsin/metabolism , Trypsin/chemistry , Nanotubes/chemistry , Stereoisomerism , Biocatalysis , Cyclohexanones/chemistryABSTRACT
The lipase from Burkholderia cepacia (BCL) was immobilized through physical adsorption on pristine and functionalized multiwalled carbon nanotubes (MWCNTs) with carboxyl or amine groups and used in the stereoselective acylation of (R,S)-1-octen-3-ol (1) and (R,S)-(E)-4-phenyl-3-buten-2-ol (4) with vinyl acetate. All immobilized preparations produced better results than free BCL. For (R,S)-4, 50% conversion and E > 200 were obtained in n-hexane or in solvent-free medium. For (R,S)-1, in solvent-free medium, the conversion was 38% with a slight increase in the E-value (E = 10).
