Improvement of the enantioselectivity of lipase catalyzed reactions with deoxycholic acid-based molecular tweezers

BACKGROUND: Lipase as a hydrolase has important applications in the synthesis of chiral drugs. Based on the special interfacial activity of lipase, bile salt as a biosurfactant can effectively improve the catalytic activity of lipase. RESULTS: In this work, the strong selective recognition of the molecular tweezers and guest molecules helps improve the guest molecule concentration near the lipase catalytic center. However, this strong recognition will also make it difficult for the guest molecules to break away from the molecular tweezers. Therefore, there is an optimal value for this recognition that can effectively improve the chiral resolution effect of lipase. CONCLUSIONS: The two hydroxyl groups on deoxycholic acid were modified to prepare deoxycholic acid-based molecular tweezers with two `arms' and one `crack.' The recognition performance between the molecular tweezers and amino acid methyl ester was determined by UV spectrophotometry. According to the binding constant, Ka, and free energy, -.G0, a complex formed between the deoxycholic acid-based molecular tweezers (host) and amino acid methyl ester (guest) due to chiral recognition. Molecular tweezers were subsequently mixed with porcine pancreatic lipase (PPL) and candida rugosa lipase (CRL), respectively, to catalyze the transesterification of racemic tryptophan methyl ester. (c) 2023 Society of Chemical Industry.