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Engineering Orthogonal Methyltransferases to Create Alternative Bioalkylation Pathways.

Abigail J Herbert1, Sarah A Shepherd1, Victoria A Cronin1

  • 1Department of Chemistry and Manchester Institute of Biotechnology, The University of Manchester, 131 Princess Street, Manchester, M1 7DN, UK.

Angewandte Chemie (International Ed. in English)
|May 14, 2020
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Summary

Researchers engineered methyltransferases (MTs) to use a novel carboxy-SAM (cxSAM) cofactor for carboxymethylation. This breakthrough enables more efficient and selective enzymatic synthesis of complex molecules.

Keywords:
bioalkylationbiotransformationscarboxymethylationenzyme cofactorsmethyltransferases

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Area of Science:

  • Biochemistry
  • Enzymology
  • Synthetic Biology

Background:

  • S-adenosyl-l-methionine (SAM)-dependent methyltransferases (MTs) are crucial enzymes catalyzing methylation reactions.
  • Rare carboxymethylation pathways utilize a carboxy-SAM (cxSAM) cofactor, generated by cxSAM synthase (CmoA).

Purpose of the Study:

  • To investigate the ability of MT enzymes to utilize cxSAM for carboxymethylation.
  • To engineer MTs for improved catalytic activity and selectivity towards cxSAM.
  • To develop novel enzymatic approaches for cofactor generation and substrate modification.

Main Methods:

  • Site-directed mutagenesis to create orthogonal MTs with enhanced cxSAM specificity.
  • Coupling engineered MTs with CmoA for efficient carboxymethylation.
  • Enzymatic generation of a new cofactor, carboxy-S-adenosyl-l-ethionine (cxSAE).

Main Results:

  • Demonstrated MTs can catalyze the carboxymethylation of tetrahydroisoquinoline (THIQ) and catechol substrates using cxSAM.
  • Engineered MTs exhibited improved catalytic activity and selectivity for cxSAM.
  • Successful coupling of engineered MTs with CmoA led to enhanced carboxymethylation efficiency.
  • Developed a method to generate cxSAE for stereoselective transfer of a chiral 1-carboxyethyl group.

Conclusions:

  • Engineered MTs can be adapted to utilize cxSAM for novel carboxymethylation reactions.
  • This work expands the enzymatic toolkit for synthesizing complex molecules with high selectivity.
  • The development of cxSAE opens new avenues for chiral synthesis using enzymatic methods.