Oxidation of glycerol by 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) in the presence of laccase.
Glycerol has the potential of being a low-cost and extremely versatile building block. However, current transformation strategies such based on noble-metal-catalysts show several disadvantages including catalyst deactivation or negative environmental impacts. In this study glycerol was oxidized by 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) in the presence of laccase from Trametes hirsuta. Analysis of the reaction production indicated sequential oxidation to glyceraldehyde, glyceric acid and tartronic acid, finally resulting in mesoxalic acid. The number and nature of oxidation products was depended on the concentration of TEMPO used. At lower TEMPO concentrations (<6mM) the major initial reaction product was glyceraldehyde while at higher concentration in addition considerable amounts of glyceric acid were formed. Glycerol oxidation was also shown with laccase immobilised on alumina pellets which increased laccase stability.
Liebminger
Stefan
S
Research Centre Applied Biocatalysis Graz, Petersgasse 14, Graz, Austria.
Siebenhofer
Matthäus
M
Guebitz
Georg
G
D005985:Glyceraldehyde / Q000378:metabolism; D005988:Glyceric Acids / Q000378:metabolism; D005990:Glycerol / Q000737:chemistry / Q000378:metabolism*; D006863:Hydrogen-Ion Concentration; D042845:Laccase / Q000378:metabolism*; D010084:Oxidation-Reduction; D010880:Piperidines / Q000737:chemistry / Q000378:metabolism*; D055454:Trametes / Q000201:enzymology*
C528764:2,2,6,6-tetramethyl-1-piperidine; D005988:Glyceric Acids; D010880:Piperidines; D005985:Glyceraldehyde; C042971:glyceric acid; D042845:Laccase; D005990:Glycerol