Amination of ω-Functionalized Aliphatic Primary Alcohols by a Biocatalytic Oxidation–Transamination Cascade
نویسندگان
چکیده
Amination of non-activated aliphatic fatty alcohols to the corresponding primary amines was achieved through a five-enzyme cascade reaction by coupling a long-chain alcohol oxidase from Aspergillus fumigatus (LCAO_Af) with a ω-transaminase from Chromobacterium violaceum (ω-TA_Cv). The alcohol was oxidized at the expense of molecular oxygen to yield the corresponding aldehyde, which was subsequently aminated by the PLP-dependent ω-TA to yield the final primary amine product. The overall cascade was optimized with respect to pH, O2 pressure, substrate concentration, decomposition of H2O2 (derived from alcohol oxidation), NADH regeneration, and biocatalyst ratio. The substrate scope of this concept was investigated under optimized conditions by using terminally functionalized C4-C11 fatty primary alcohols bearing halogen, alkyne, amino, hydroxy, thiol, and nitrile groups.
منابع مشابه
Aliphatic alcohols oxidation with Hydrogen Peroxide in water catalyzed by supported Phosphotungstic acid (PTA) on Silica coated MgAl2O4 nanoparticles as a recoverable catalyst
In this paper, a novel catalyst (MgAl2O4@SiO2-PTA) was proposed for the green oxidation of aliphatic alcohols. The resultant composite was characterized by different techniques, such as X-ray diffraction (XRD), SEM, FT-IR, EDX and Brunauer-Emmett-Teller (BET) surface area analysis. The prepared nanocomposite was used as a catalyst for oxidation of aliphatic alco...
متن کاملAliphatic alcohols oxidation with Hydrogen Peroxide in water catalyzed by supported Phosphotungstic acid (PTA) on Silica coated MgAl2O4 nanoparticles as a recoverable catalyst
In this paper, a novel catalyst (MgAl2O4@SiO2-PTA) was proposed for the green oxidation of aliphatic alcohols. The resultant composite was characterized by different techniques, such as X-ray diffraction (XRD), SEM, FT-IR, EDX and Brunauer-Emmett-Teller (BET) surface area analysis. The prepared nanocomposite was used as a catalyst for oxidation of aliphatic alco...
متن کاملThe Industrial Age of Biocatalytic Transamination
During the last decade the use of ω-transaminases has been identified as a very powerful method for the preparation of optically pure amines from the corresponding ketones. Their immense potential for the preparation of chiral amines, together with their ease of use in combination with existing biocatalytic methods, have made these biocatalysts a competitor to any chemical methodology for (asym...
متن کاملEpoxidation of Alkenes and Oxidation of Alcohols with Hydrogen Peroxide Catalyzed by a Fe (Br8TPPS) Supported on Amberlite IRA-400
Iron (III) meso-tetrakis(p-sulfonatophenyl)-β-octabromoporphyrin supported on Amberlite IRA- 400 [Fe(Br8 TPPS)-Ad-400] is a robust and efficient catalyst for oxidation of alkenes and alcohols at room temperature. The catalyst exhibits a high activity and stability in hydrocarbon oxidation by H2 O2 . The method was useful in the oxidation of various primary, secondary-aliphatic, alicyclic and ar...
متن کاملNitrogen functionalized carbon nanostructures supported Pd and Au-Pd NPs as catalyst for alcohols oxidation
Two different carbon nanotubes (CNTs) PR24-PS and Baytubes were functionalized by oxidation with nitric acid and further amination with gaseous NH3. Thus Au and Au-Pd nanoparticles were prepared by PVA/NaBH4 system and anchored on the surface of pristine CNTs and NCNTs (Nitrogen functionalized carbon nanotubes). TEM analysis revealed that the introduction of nitrogen functionalities improves th...
متن کامل