TY - JOUR
T1 - Lipase-Catalysed Enzymatic Kinetic Resolution of Aromatic Morita-Baylis-Hillman Derivatives by Hydrolysis and Transesterification
AU - Mathebula, Nompumelelo P.
AU - Sheldon, Roger A.
AU - Bode, Moira L.
PY - 2022
Y1 - 2022
N2 - Acylated Morita-Baylis-Hillman (MBH) adducts were synthesised and subjected to enzymatic kinetic resolution (EKR) by hydrolysis employing various lipase enzymes: from P. fluorescens, P. cepacia (PCL), C. antarctica A (CAL−A), C. antarctica B (CAL−B) and Novozyme 435. In a number of instances enantiopure Morita-Baylis-Hillman acetates or butyrates and their corresponding hydrolysed MBH adducts were obtained with ee values of >90 %, at ca. 50 % conversion, corresponding to enantiomeric ratio (E) values of >200. Enantioselective transesterification reactions on MBH adducts was achieved using acyl anhydrides in THF or the greener organic solvent 2-MeTHF in the presence of CAL−A. This is the first report of successful lipase-catalysed EKR of aromatic MBH adducts by transesterification in organic medium.
AB - Acylated Morita-Baylis-Hillman (MBH) adducts were synthesised and subjected to enzymatic kinetic resolution (EKR) by hydrolysis employing various lipase enzymes: from P. fluorescens, P. cepacia (PCL), C. antarctica A (CAL−A), C. antarctica B (CAL−B) and Novozyme 435. In a number of instances enantiopure Morita-Baylis-Hillman acetates or butyrates and their corresponding hydrolysed MBH adducts were obtained with ee values of >90 %, at ca. 50 % conversion, corresponding to enantiomeric ratio (E) values of >200. Enantioselective transesterification reactions on MBH adducts was achieved using acyl anhydrides in THF or the greener organic solvent 2-MeTHF in the presence of CAL−A. This is the first report of successful lipase-catalysed EKR of aromatic MBH adducts by transesterification in organic medium.
KW - enzymatic kinetic resolution
KW - lipases
KW - molecular modelling
KW - Morita-Baylis-Hillman
KW - Mosher derivatives
KW - PCL
UR - http://www.scopus.com/inward/record.url?scp=85138887666&partnerID=8YFLogxK
U2 - 10.1002/cbic.202200435
DO - 10.1002/cbic.202200435
M3 - Article
C2 - 36049111
AN - SCOPUS:85138887666
SN - 1439-4227
VL - 23
JO - ChemBioChem
JF - ChemBioChem
IS - 21
M1 - e202200435
ER -