Calculated ionisation potentials determine the oxidation of vanillin precursors by lignin peroxidase.
In view of the biocatalytic production of vanillin, this research focused on the lignin peroxidase (LiP) catalysed oxidation of naturally occurring phenolic derivatives: O-methyl ethers, O-acetyl esters, and O-glucosyl ethers. The ionisation potential (IP) of a series of model compounds was calculated and compared to their experimental conversion by LiP, defining a relative IP threshold of approximately 9.0 eV. Based on this threshold value only the O-acetyl esters and glucosides of isoeugenol and coniferyl alcohol would be potential LiP substrates. Both O-acetyl esters were tested and were shown to be converted to O-acetyl vanillin in molar yields of 51.8 and 2.3%, respectively.
Department of Food Technology and Nutritional Sciences, Wageningen Agricultural University, The Netherlands. Rimko.tenHave@algemeen.im.wau.nl
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R
ten Have
I M
IM
Rietjens
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S
Hartmans
H J
HJ
Swarts
J A
JA
Field
D001547:Benzaldehydes / Q000138:chemical synthesis*; D004583:Electrons; D004987:Ethers / Q000138:chemical synthesis / Q000737:chemistry*; D010084:Oxidation-Reduction; D010544:Peroxidases / Q000737:chemistry*; D013379:Substrate Specificity
D001547:Benzaldehydes; D004987:Ethers; C100058:vanillin; D010544:Peroxidases; C042858:lignin peroxidase