Direct biocatalytic one-pot-transformation of cyclohexanol with molecular oxygen into ɛ-caprolactone.
The development of a biocatalytic process concept for ɛ-caprolactone, which directly converts cyclohexanol as an easily available industrial raw material into the desired ɛ-caprolactone in a one-pot fashion while only requiring air as sole reagent, is reported. The desired product ɛ-caprolactone was obtained with 94-97% conversion when operating at a substrate concentration in the range of 20-60 mM. At higher substrate concentrations, however, a significant drop of conversion was found. Subsequent detailed studies on the impact of the starting material, intermediate and product components revealed a significant inhibition and partial deactivation of the BVMO by the product ɛ-caprolactone (in particular at higher concentrations) as well as an inhibition of the BVMO by cyclohexanol and cyclohexanone.
Department of Chemistry and Pharmacy, University of Erlangen-Nürnberg, Germany.
Svenja
S
Staudt
Uwe T
UT
Bornscheuer
Ulf
U
Menyes
Werner
W
Hummel
Harald
H
Gröger
D016954:Acinetobacter calcoaceticus / Q000201:enzymology; D001426:Bacterial Proteins / Q000378:metabolism; D055162:Biocatalysis; D019149:Bioreactors; D001709:Biotechnology; D001711:Biotransformation; D002208:Caproates / Q000378:metabolism*; D003511:Cyclohexanols / Q000378:metabolism*; D004795:Enzyme Stability; D007783:Lactones / Q000378:metabolism*; D010100:Oxygen / Q000378:metabolism; D010105:Oxygenases / Q000037:antagonists & inhibitors / Q000378:metabolism
D001426:Bacterial Proteins; D002208:Caproates; D003511:Cyclohexanols; D007783:Lactones; C121056:caprolactone; D010105:Oxygenases; C019961:cyclohexanone oxygenase; D010100:Oxygen
ADH; Alcohol dehydrogenase; BVMO; Baeyer–Villiger monooxygenase; Cyclohexanol; Cyclohexanone; LK-ADH; Oxidation; UCC; Union Carbide Corporation; alcohol dehydrogenase; alcohol dehydrogenase from Lactobacillus kefir; ɛ-Caprolactone