Comparative S -adenosyl-L-methionine analogue generation for selective biocatalytic Friedel-Crafts alkylation

Methyltransferases provide excellent specificity in late-stage alkylation of biomolecules. Their dependence on -adenosyl-L-methionine (SAM) mandates efficient access to SAM analogues for biocatalytic applications. We directly compared halide methyltransferase (HMT) and methionine adenosyltransferase...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2023-05, Vol.59 (36), p.5463-5466
Main Authors: Hoffmann, Arne, Schülke, Kai H, Hammer, Stephan C, Rentmeister, Andrea, Cornelissen, Nicolas V
Format: Article
Language:English
Subjects:
Alkylation
Biocatalysis
Biomolecules
Cascade chemical reactions
Coumarin
Friedel-Crafts reaction
Methionine
Methionine Adenosyltransferase - metabolism
Methylation
Methyltransferases - metabolism
S-Adenosylmethionine - metabolism
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Summary:Methyltransferases provide excellent specificity in late-stage alkylation of biomolecules. Their dependence on -adenosyl-L-methionine (SAM) mandates efficient access to SAM analogues for biocatalytic applications. We directly compared halide methyltransferase (HMT) and methionine adenosyltransferase (MAT) to access SAM analogues and explored their utility in cascade reactions with NovO for regioselective, late-stage Friedel-Crafts alkylation of a coumarin. The HMT cascade efficiently provided SAM for methylation, while the MAT cascade also supplied high levels of SAM analogues for alkylation reactions.
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc01036h