TY - JOUR
T1 - Influence of Reaction Conditions on Enzymatic Enantiopreference
T2 - the Curious Case of HEwT in the Synthesis of THF-Amine
AU - Heckmann, Christian M.
AU - Robustini, Lucia
AU - Paradisi, Francesca
PY - 2022
Y1 - 2022
N2 - 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.
AB - 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.
KW - amines
KW - biocatalysis
KW - enantioselectivity
KW - enzyme
KW - THF ketones
KW - transaminases
UR - http://www.scopus.com/inward/record.url?scp=85133201063&partnerID=8YFLogxK
U2 - 10.1002/cbic.202200335
DO - 10.1002/cbic.202200335
M3 - Article
C2 - 35705492
AN - SCOPUS:85133201063
SN - 1439-4227
VL - 23
JO - ChemBioChem
JF - ChemBioChem
IS - 15
M1 - e202200335
ER -