Thebaine is Selectively Demethylated by Thebaine 6-O-Demethylase and Codeine-3-O-demethylase at Distinct Binding Sites: A Computational Study Article Swipe
Warispreet Singh
,
Chenggong Hui
,
Chun Li
,
Meilan Huang
·
YOU?
·
· 2021
· Open Access
·
· DOI: https://doi.org/10.1021/acs.inorgchem.1c00468
YOU?
·
· 2021
· Open Access
·
· DOI: https://doi.org/10.1021/acs.inorgchem.1c00468
Two homologous 2-oxoglutarate-dependent (ODD) nonheme enzymes thebaine 6-O-demethylase (T6ODM) and codeine-3-O-demethylase (CODM), are involved in the morphine biosynthesis pathway from thebaine, catalyzing the O-demethylation reaction with precise regioselectivity at C6 and C3 positions of thebaine respectively. We investigated the origin of the regioselectivity of these enzymes by combined molecular dynamics (MD) and quantum mechanics/molecular mechanics (QM/MM) calculations and found that Thebaine binds at the two distinct sites of T6ODM and CODM, which determines the regioselectivity of the enzymes. A remarkable oxo rotation is observed in the decarboxylation process. Starting from the closed pentacoordinate configuration, the C-terminal lid adopts an open conformation in the octahedral Fe(IV) = O complex to facilitate the subsequent demethylation. Phe241 and Phe311 stabilize the substrate in the binding pocket, while Arg219 acts as a gatekeeper residue to stabilize the substrate. Our results unravel the regioselectivity in 2-OG dependent nonheme enzymes and may shed light for exploring the substrate scope of these enzymes and developing novel biotechnology for morphine biosynthesis.
Related Topics
Concepts
Chemistry
Thebaine
Regioselectivity
Demethylase
Stereochemistry
Molecular mechanics
Enzyme
Biosynthesis
Demethylation
Molecular dynamics
Biochemistry
Morphine
Computational chemistry
Catalysis
Codeine
Histone
Medicine
Gene expression
Pharmacology
Gene
DNA methylation
Metadata
- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1021/acs.inorgchem.1c00468
- OA Status
- green
- Cited By
- 8
- References
- 62
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W3174035912
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
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https://openalex.org/W3174035912Canonical identifier for this work in OpenAlex
- DOI
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https://doi.org/10.1021/acs.inorgchem.1c00468Digital Object Identifier
- Title
-
Thebaine is Selectively Demethylated by Thebaine 6-O-Demethylase and Codeine-3-O-demethylase at Distinct Binding Sites: A Computational StudyWork title
- Type
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articleOpenAlex work type
- Language
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enPrimary language
- Publication year
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2021Year of publication
- Publication date
-
2021-07-02Full publication date if available
- Authors
-
Warispreet Singh, Chenggong Hui, Chun Li, Meilan HuangList of authors in order
- Landing page
-
https://doi.org/10.1021/acs.inorgchem.1c00468Publisher landing page
- Open access
-
YesWhether a free full text is available
- OA status
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greenOpen access status per OpenAlex
- OA URL
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https://pure.qub.ac.uk/en/publications/dd14402b-59da-4106-a867-2afc54626079Direct OA link when available
- Concepts
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Chemistry, Thebaine, Regioselectivity, Demethylase, Stereochemistry, Molecular mechanics, Enzyme, Biosynthesis, Demethylation, Molecular dynamics, Biochemistry, Morphine, Computational chemistry, Catalysis, Codeine, Histone, Medicine, Gene expression, Pharmacology, Gene, DNA methylationTop concepts (fields/topics) attached by OpenAlex
- Cited by
-
8Total citation count in OpenAlex
- Citations by year (recent)
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2025: 4, 2024: 2, 2023: 1, 2022: 1Per-year citation counts (last 5 years)
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62Number of works referenced by this work
- Related works (count)
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10Other works algorithmically related by OpenAlex
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