Candida antarctica Lipase A-Based Enantiorecognition of a Highly Strained 4-Dibenzocyclooctynol (DIBO) Used for PET Imaging
Sirén, S., Dahlström, K. M., Puttreddy, R., Rissanen, K., Salminen, T. A., Scheinin, M., Li, X.-G., & Liljeblad, A. (2020). Candida antarctica Lipase A-Based Enantiorecognition of a Highly Strained 4-Dibenzocyclooctynol (DIBO) Used for PET Imaging. Molecules, 25(4), Article 879. https://doi.org/10.3390/molecules25040879
© 2020 by the authors. Licensee MDPI, Basel, Switzerland.
The enantiomers of aromatic 4-dibenzocyclooctynol (DIBO), used for radiolabeling and subsequent conjugation of biomolecules to form radioligands for positron emission tomography (PET), were separated by kinetic resolution using lipase A from Candida antarctica (CAL-A). In optimized conditions, (R)-DIBO [(R)-1, ee 95%] and its acetylated (S)-ester [(S)-2, ee 96%] were isolated. In silico docking results explained the ability of CAL-A to differentiate the enantiomers of DIBO and to accommodate various acyl donors. Anhydrous MgCl2 was used for binding water from the reaction medium and, thus, for obtaining higher conversion by preventing hydrolysis of the product (S)-2 into the starting material. Since the presence of hydrated MgCl26H2O also allowed high conversion or effect on enantioselectivity, Mg2+ ion was suspected to interact with the enzyme. Binding site predictions indicated at least two sites of interest; one in the lid domain at the bottom of the acyl binding pocket and another at the interface of the hydrolase and flap domains, just above the active site. ...
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Related funder(s)Academy of Finland
Funding program(s)Postdoctoral Researcher, AoF
Additional information about fundingThe authors thank Turku University Foundation for financial support. SS received financial support from the National Graduate School in Informational and Structural Biology, hosted by Åbo Akademi University, Finland. TAS and KMD acknowledge the Biocenter Finland technology platforms of bioinformatics (J.V. Lehtonen), translational activities and structural biology (Instruct-FI) at the Structural Bioinformatics Laboratory. TAS and KMD also thank the CSC IT Center for Science for laboratory and computational infrastructure support. This work was supported by the Sigrid Juselius Foundation (TAS, KMD) and Tor, Joe, and Pentti Borg’s Foundation (TAS). The authors gratefully acknowledge financial support from the Academy of Finland (RP: grant no. 298817) and the University of Jyväskylä. ...
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