Unlocking Lactonase Enzymes as Biocatalysts for the Deracemisation of Chiral γ‐Thiolactones Article Swipe
Jingyue Wu
,
Michele Crotti
,
Ivan Bassanini
,
Mahdi Hassankalhori
,
Erica Elisa Ferrandi
,
Ferran Sancho
,
Daniela Monti
,
Daniele Castagnolo
·
YOU?
·
· 2025
· Open Access
·
· DOI: https://doi.org/10.1002/anie.202505032
YOU?
·
· 2025
· Open Access
·
· DOI: https://doi.org/10.1002/anie.202505032
Lactonases, a class of metalloenzymes that exhibit catalytic promiscuity, have been extensively studied from a biological perspective, yet their application as biocatalysts remains underexplored. In this study, we disclose the biocatalytic activity of lactonase enzymes in the hydrolysis and deracemisation of chiral C3‐substituted‐γ‐thiolactones and the asymmetric synthesis of γ‐thio‐α‐substituted‐carboxylic acids. The thiolactonase activity of lactonases from different protein superfamilies was investigated. The biocatalyst GcL, from the metallo‐β‐lactamase‐like lactonase family, catalysed the enzymatic kinetic resolution (EKR) of homocysteine (Hcy) thiolactones with excellent enantioselectivity ( E ‐value up to 136), yielding enantioenriched Hcy thiolactones and γ‐thio‐α‐amino‐carboxylic acids with high ees. Additionally, the biocatalyst N9 Y71G, a rationally engineered variant of the reconstructed ancestral paraoxonase enzyme N9, catalysed the dynamic kinetic resolution (DKR) of C3‐thio‐γ‐thiolactones, yielding γ‐thio‐α‐thio‐carboxylic acids in enantioselective manner with high ees (up to >99%) and yields (up to >99%). Insights on the mechanism and the stereoselectivity of the lactonase biocatalysts were gained through computational and site‐directed mutagenesis studies.
Related Topics
Concepts
Biocatalysis
Thio-
Chemistry
Kinetic resolution
Enantioselective synthesis
Enzyme
Stereochemistry
Amino acid
Combinatorial chemistry
Catalysis
Biochemistry
Reaction mechanism
Metadata
- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1002/anie.202505032
- https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/anie.202505032
- OA Status
- hybrid
- References
- 83
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W4410113512
All OpenAlex metadata
Raw OpenAlex JSON
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https://openalex.org/W4410113512Canonical identifier for this work in OpenAlex
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https://doi.org/10.1002/anie.202505032Digital Object Identifier
- Title
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Unlocking Lactonase Enzymes as Biocatalysts for the Deracemisation of Chiral γ‐ThiolactonesWork title
- Type
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articleOpenAlex work type
- Language
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enPrimary language
- Publication year
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2025Year of publication
- Publication date
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2025-05-06Full publication date if available
- Authors
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Jingyue Wu, Michele Crotti, Ivan Bassanini, Mahdi Hassankalhori, Erica Elisa Ferrandi, Ferran Sancho, Daniela Monti, Daniele CastagnoloList of authors in order
- Landing page
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https://doi.org/10.1002/anie.202505032Publisher landing page
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https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/anie.202505032Direct link to full text PDF
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YesWhether a free full text is available
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hybridOpen access status per OpenAlex
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https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/anie.202505032Direct OA link when available
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Biocatalysis, Thio-, Chemistry, Kinetic resolution, Enantioselective synthesis, Enzyme, Stereochemistry, Amino acid, Combinatorial chemistry, Catalysis, Biochemistry, Reaction mechanismTop concepts (fields/topics) attached by OpenAlex
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0Total citation count in OpenAlex
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