Influence of Reaction Conditions on Enzymatic Enantiopreference: the Curious Case of HEwT in the Synthesis of THF-Amine

Christian M. Heckmann, Lucia Robustini, Francesca Paradisi*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

3 Citations (Scopus)

Abstract

Enzymatic enantiopreference is one of the key advantages of biocatalysis. While exploring the synthesis of small cyclic (chiral amines) such as 3-aminotetrahydrofuran (THF-amine), using the (S)-selective transaminase from Halomonas elongata (HEwT), inversion of the enantiopreference was observed at increasing substrate loadings. In addition, the enantiopreference could be altered by variation of the ionic strength, or of the co-solvent content in the reaction mixture. For example, using otherwise identical reaction conditions, the presence of 2 M sodium chloride gave (R)-THF-amine (14 % ee), while the addition of 2.2 M isopropyl alcohol gave the (S)-enantiomer in 30 % ee. While the underlying cause is not currently understood, it appears likely that subtle changes in the structure of the enzyme cause the shift in enantiopreference and are worth exploring further.

Original languageEnglish
Article numbere202200335
Number of pages6
JournalChemBioChem
Volume23
Issue number15
DOIs
Publication statusPublished - 2022
Externally publishedYes

Keywords

  • amines
  • biocatalysis
  • enantioselectivity
  • enzyme
  • THF ketones
  • transaminases

Fingerprint

Dive into the research topics of 'Influence of Reaction Conditions on Enzymatic Enantiopreference: the Curious Case of HEwT in the Synthesis of THF-Amine'. Together they form a unique fingerprint.

Cite this