Lipase-mediated epoxidation of alkenes in supercritical carbon dioxide

ABSTRACT

In this work, supercritical carbon dioxide was used as reaction media in the lipase-mediated epoxidation of alkenes for the first time. Under the optimal conditions (alkene (1 mmol), novozym 435 (15 mg), H₂O₂ (50% aqueous solution, 1.4 mmol), n-caprylic acid (0.05 mmol), 40°C, scCO₂ (10 MPa, 25 mL)), high yields (83–98%) of epoxidation of alkenes could be obtained in a short reaction time. Furthermore, novozym 435 exhibited a satisfactory reusability in the epoxidations. Thus, this work not only presents a green and mild method of lipase-mediated epoxidation with higher yield and reaction rate than other lipase-mediated routes ever reported but also expands the application of supercritical carbon dioxide in enzyme catalytic promiscuity.

GRAPHICAL ABSTRACT

KEYWORDS:

• Lipase
• catalytic promiscuity
• epoxidation
• alkenes
• supercritical carbon dioxide

Acknowledgments

We gratefully acknowledge the Foundation of Changchun BC&HC Pharmaceutical Technology Co., Ltd (no. 3R117W391465).

Disclosure statement

No potential conflict of interest was reported by the authors.

Notes on contributors

Jiaxin Zhang is studying as a master candidate in School of Life Sciences, Jilin University. Her research has focused on the biocatalysis in unconventional reaction media.

Wenwei Qian is studying as an undergraduate in School of Life Sciences, Jilin University. Her research has focused on the biocatalysis in unconventional reaction media.

Chunyu Wang is working at State Key Laborarory of Supramolecular Structure and Materials, Jilin University. His research has focused on the synthesis of bioactive compounds.

Ziyi Cao is studying as an undergraduate in School of Life Sciences, Jilin University. Her research has focused on the biocatalysis in unconventional reaction media.

Shanshan Chen is studying as an undergraduate in School of Life Sciences, Jilin University. Her research has focused on the synthesis and development of new drugs.

Liu Zhang is studying as a master candidate in School of Life Sciences, Jilin University. Her research has focused on the biocatalysis and biotransformation.

Yang Zhang is working at Department of Biopharmacy, School of Pharmaceutical Sciences, Jilin University. Now, she is mainly investigating the biological activity of chiral drugs.

Lei Wang is working in Key Laboratory of Molecular Enzymology and Engineering of Ministry of Education, Jilin University as a professor. Recently, his research has focused on the new synthetic methodologies to synthesize bioactive compounds.