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Record W4402668948 · doi:10.1016/j.jbc.2024.107809

Characterization of a cytochrome P450 that catalyzes the O-demethylation of lignin-derived benzoates

2024· article· en· W4402668948 on OpenAlexafffund
Megan E Wolf, D.J. Hinchen, J.E. McGeehan, Lindsay D. Eltis

Bibliographic record

VenueJournal of Biological Chemistry · 2024
Typearticle
Languageen
FieldChemistry
TopicMetal-Catalyzed Oxygenation Mechanisms
Canadian institutionsUniversity of British Columbia
FundersNational Renewable Energy LaboratoryResearch EnglandNatural Sciences and Engineering Research Council of CanadaU.S. Department of EnergyDiamond Light SourceUniversity of Portsmouth
KeywordsDemethylationBenzoatesMonooxygenaseChemistryRhodococcusCytochrome P450LigninStereochemistryReductaseBiochemistryEnzymeBond cleavageOrganic chemistryGeneCatalysis

Abstract

fetched live from OpenAlex

Cytochromes P450 (P450s) are a superfamily of heme-containing enzymes possessing a broad range of monooxygenase activities. One such activity is O -demethylation, an essential and rate-determining step in emerging strategies to valorize lignin that employ carbon–carbon bond cleavage. We recently identified PbdA, a P450 from Rhodococcus jostii RHA1, and PbdB, its cognate reductase, which catalyze the O -demethylation of para -methoxylated benzoates ( p -MBAs) to initiate growth of RHA1 on these compounds. PbdA had the highest affinity ( K d = 3.8 ± 0.6 μM) and apparent specificity ( k cat / K M = 20,000 ± 3000 M -1 s -1 ) for p- MBA. The enzyme also O -demethylated two related lignin-derived aromatic compounds with remarkable efficiency: veratrate and isovanillate. PbdA also catalyzed the hydroxylation and dehydrogenation of p- ethylbenzoate even though RHA1 did not grow on this compound. Atomic-resolution structures of PbdA in complex with p -MBA, p- ethylbenzoate, and veratrate revealed a cluster of three residues that form hydrogen bonds with the substrates' carboxylate: Ser87, Ser237, and Arg84. Substitution of these residues resulted in lower affinity and O -demethylation activity on p -MBA as well as increased affinity for the acetyl analog, p- methoxyacetophenone. The S87A and S237A variants of PbdA also catalyzed the O -demethylation of an aldehyde analog of p -MBA, p -methoxy-benzaldehyde, while the R84M variant did not, despite binding this compound with high affinity. These results suggest that Ser87, Ser237, and Arg84 are not only important determinants of specificity but also help to orientate that substrate correctly in the active site. This study facilitates the design of biocatalysts for lignin valorization.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.001
metaresearch head score (Gemma)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.002
Threshold uncertainty score0.904

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0010.000

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.035
GPT teacher head0.258
Teacher spread0.223 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one teacher head, not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designBench or experimental
Domainnot available
GenreEmpirical

How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".

Quick stats

Citations12
Published2024
Admission routes2
Has abstractyes

Explore more

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