A1 Journal article (refereed)
Multienzymatic Synthesis of γ‐Lactam Building Blocks from Unsaturated Esters and Hydroxylamine (2023)

Jäger, C., Nieger, M., Rissanen, K., & Deska, J. (2023). Multienzymatic Synthesis of γ‐Lactam Building Blocks from Unsaturated Esters and Hydroxylamine. European Journal of Organic Chemistry, 26(39), Article e202300288. https://doi.org/10.1002/ejoc.202300288

JYU authors or editors

Publication details

All authors or editorsJäger, Christina; Nieger, Martin; Rissanen, Kari; Deska, Jan

Journal or seriesEuropean Journal of Organic Chemistry



Publication year2023

Publication date07/08/2023


Issue number39

Article numbere202300288

PublisherWiley-VCH Verlag

Publication countryGermany

Publication languageEnglish


Publication open accessOpenly available

Publication channel open accessPartially open access channel

Publication is parallel published (JYX)https://jyx.jyu.fi/handle/123456789/88928


The assembly of enzymatic cascades and multi-step reaction sequences represents an attractive alternative to traditional synthetic-organic approaches. The biocatalytic reaction mediators offer not only mild conditions and permit the use of environmentally benign reagents, but the high compatibility of different enzymes promises more streamlined reaction setups. In this study, a triple-enzymatic strategy was developed that enables the direct conversion of γ,δ-unsaturated esters to N-hydroxy-γ-lactame building blocks. Hereby, a lipase-catalyzed hydroxylaminolysis generates hydroxamic acid intermediates that are subsequently aerobically activated by horseradish peroxidase and glucose oxidase to cyclize in an intramolecular nitroso ene reaction. Utilizing the hydroxyl­aminolysis/ene-cyclization sequence for the preparation of an aza-spirocyclic lactam, the multi-enzymatic methodology was successfully employed in the synthesis of key intermediates en route to alkaloids of the Cephalotaxus family.

Keywordsenzymesorganic chemistryorganic compounds

Contributing organizations

Ministry reportingYes

Reporting Year2023

Preliminary JUFO rating1

Last updated on 2024-03-04 at 18:35