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Protein engineering created a new enzyme variant for biocatalytic Friedel-Crafts acylation. This variant broadens substrate scope, enabling efficient synthesis of acetophenone derivatives from diverse activated esters.

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Area of Science:

  • Biocatalysis
  • Organic Chemistry
  • Enzyme Engineering

Background:

  • Friedel-Crafts acylation is a key organic reaction.
  • Biocatalytic approaches offer sustainable alternatives.
  • Acyltransferases can catalyze Friedel-Crafts acylation using activated esters.

Purpose of the Study:

  • To engineer an acyltransferase with an extended substrate scope for Friedel-Crafts acylation.
  • To enable the synthesis of a wider range of acetophenone derivatives.

Main Methods:

  • Rational protein engineering of an acyltransferase.
  • Identification of key active site residues.
  • Site-directed mutagenesis to create enzyme variants.

Main Results:

  • A single-point variant (F148V) was successfully generated.
  • The F148V variant accepted medium chain length alkyl and alkoxyalkyl carboxylic esters as donor substrates.
  • High conversions (up to 99%) and isolated yields (up to >99%) were achieved.

Conclusions:

  • Protein engineering can significantly enhance enzyme capabilities for biocatalysis.
  • The engineered acyltransferase variant expands the synthetic utility of biocatalytic Friedel-Crafts acylation.
  • This work provides a platform for synthesizing novel acetophenone derivatives.