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Regiocomplementary O-methylation of catechols by using three-enzyme cascades

: Siegrist, Jutta; Aschwanden, Simon; Mordhorst, Silja; Thöny-Meyer, Linda; Richter, Michael; Andexer, Jennifer N.


ChemBioChem 16 (2015), No.18, pp.2576-2579
ISSN: 1439-4227
ISSN: 1439-7633
Journal Article
Fraunhofer IGB ()

S-Adenosylmethionine (SAM)-dependent enzymes have great potential for selective alkylation processes. In this study we investigated the regiocomplementary O-methylation of catechols. Enzymatic methylation is often hampered by the need for a stoichiometric supply of SAM and the inhibitory effect of the SAM-derived byproduct on most methyltransferases. To counteract these issues we set up an enzyme cascade. Firstly, SAM was generated from l-methionine and ATP by use of an archaeal methionine adenosyltransferase. Secondly, 4-O-methylation of the substrates dopamine and dihydrocaffeic acid was achieved by use of SafC from the saframycin biosynthesis pathway in 40–70% yield and high selectivity. The regiocomplementary 3-O-methylation was catalysed by catechol Omethyltransferase from rat. Thirdly, the beneficial influence of a nucleosidase on the overall conversion was demonstrated. The results of this study are important milestones on the pathway to catalytic SAM-dependent alkylation processes.