A1 Journal article (refereed)
Candida antarctica Lipase A-Based Enantiorecognition of a Highly Strained 4-Dibenzocyclooctynol (DIBO) Used for PET Imaging (2020)

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

JYU authors or editors

Publication details

All authors or editorsSirén, Saija; Dahlström, Käthe M.; Puttreddy, Rakesh; Rissanen, Kari; Salminen, Tiina A.; Scheinin, Mika; Li, Xiang-Guo; Liljeblad, Arto

Journal or seriesMolecules


Publication year2020


Issue number4

Article number879


Publication countrySwitzerland

Publication languageEnglish


Publication open accessOpenly available

Publication channel open accessOpen Access channel

Publication is parallel published (JYX)https://jyx.jyu.fi/handle/123456789/68001


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.

Keywordstracers (indicators)aromatic compoundsbiocatalysisnaturally occurring substancesyeast fungienzymeslipasescomputational chemistry

Free keywordsbiocatalysis; lipase A from Candida antarctica; DIBO; kinetic resolution; molecular modeling

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Ministry reportingYes

Reporting Year2020

JUFO rating1

Last updated on 2024-22-04 at 13:07