Ester Synthesis in Water: Mycobacterium smegmatis Acyl Transferase for Kinetic Resolutions

Nicolas deLeeuw, Guzman Torrelo, Carolin Bisterfeld, Verena Resch, Luuk Mestrom, Emanuele Straulino, L. Koekkoek-van der Weel, Ulf Hanefeld

Research output: Contribution to journalArticleScientificpeer-review

21 Citations (Scopus)

Abstract

The acyl transferase from Mycobacterium smegmatis (MsAcT) catalyses transesterification reactions in aqueous media because of its hydrophobic active site. Aliphatic cyanohydrin and alkyne esters can be synthesised in water with excellent and strikingly opposite enantioselectivity [(R);E>37 and (S);E>100, respectively]. When using this enzyme, the undesired hydrolysis of the acyl donor is an important factor to take into account. Finally, the choice of acyl donor can significantly influence the obtained enantiomeric excesses.

Original languageEnglish
Pages (from-to)242-249
JournalAdvanced Synthesis & Catalysis
DOIs
Publication statusPublished - 2018

Keywords

  • Acyl transferase
  • Hydrolase
  • Kinetic resolution
  • Mycobacterium smegmatis
  • Transesterification
  • Water

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