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

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

Journal Article (2018)

Author(s)

Nicolas deLeeuw (Student TU Delft)

Guzman Torrelo (Student TU Delft)

Carolin Bisterfeld (TU Delft - Applied Sciences)

Verena Resch (TU Delft - Applied Sciences)

Luuk Mestrom (TU Delft - Applied Sciences)

Emanuele Straulino (TU Delft - Applied Sciences)

L. Koekkoek-van der Weel (TU Delft - Applied Sciences)

Ulf Hanefeld (TU Delft - Applied Sciences)

Research Group

BT/Biocatalysis

Water Kinetic resolution Mycobacterium smegmatis Hydrolase Transesterification Acyl transferase

DOI related publication

https://doi.org/10.1002/adsc.201701282 Final published version

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https://resolver.tudelft.nl/uuid:cc4dc5ba-939d-41c5-8b05-778d6743e73b

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Publication Year

2018

Language

English

Research Group

BT/Biocatalysis

Pages (from-to)

242-249

Downloads counter

234

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.