Biocatalytic asymmetric synthesis of secondary allylic alcohols using Burkholderia cepacia lipase immobilized on multiwalled carbon nanotubes

Abstract

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).

A Multicomponent Mannich Reaction Catalyzed by Hydrolases Immobilized on Titanate Nanotubes

“…[24][25][26] In recent years, the immobilization method involves the incorporation of enzymes into nanostructured materials and has shown great promise for enhancing enzyme stability and activity. [27][28][29] Nanostructured materials offer unique and fascinating characteristics that balance key factors determining biocatalyst efficiency, including high surface area, which minimizes mass transfer resistance. [24,[26][27][28][29][30] In this area, nanostructured titanium dioxide (TiO 2 ) materials have excelled due to their wide applications, [31,32] low-cost preparation, regular and controllable nanoscale geometry, high specific surface area and attractive biocompatibility.…”

“…[27][28][29] Nanostructured materials offer unique and fascinating characteristics that balance key factors determining biocatalyst efficiency, including high surface area, which minimizes mass transfer resistance. [24,[26][27][28][29][30] In this area, nanostructured titanium dioxide (TiO 2 ) materials have excelled due to their wide applications, [31,32] low-cost preparation, regular and controllable nanoscale geometry, high specific surface area and attractive biocompatibility. [9,[31][32][33] Furthermore, the functional hydroxyl groups present on the surface of titanate nanotubes (NtsTi) can provide an aqueous microenvironment and stabilize the enzyme structure when used in organic solvents.…”

“…In recent years, the immobilization method involves the incorporation of enzymes into nanostructured materials and has shown great promise for enhancing enzyme stability and activity [27–29] . Nanostructured materials offer unique and fascinating characteristics that balance key factors determining biocatalyst efficiency, including high surface area, which minimizes mass transfer resistance [24,26–30] .…”