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Record W4400257847 · doi:10.26434/chemrxiv-2024-5tjrz

Indigo Formation as a Predictor of Substrate Promiscuity in Cytochrome P450 BM3 Libraries

2024· preprint· en· W4400257847 on OpenAlexafffund
Donya Valikhani, Jonathan N. Besna, Olivier Rousseau, Claudèle Lemay-St-Denis, Guillaume Lamoureux, Joelle N. Pelletier

Bibliographic record

VenueChemRxiv · 2024
Typepreprint
Languageen
FieldComputer Science
TopicComputational Drug Discovery Methods
Canadian institutionsUniversité de Montréal
FundersNatural Sciences and Engineering Research Council of CanadaCanada Research Chairs
KeywordsIndigoHydroxylationChemistryIndigo carmineCytochrome P450Saturated mutagenesisStereochemistryActive siteBiochemistryEnzymeGeneMutant

Abstract

fetched live from OpenAlex

Cytochrome P450 BM3 natively exhibits substrate promiscuity, mainly in hydroxylation and epoxidation reactions. Whereas directed evolution has broadened its scope of reactivity, screening for specific non-native enzymatic reactivity remains challenging, thereby limiting potential applications. In this study, we investigated the predictive potential of indigo production as an indicator of promiscuous hydroxylation in non-native aromatic compounds. Following site- saturation mutagenesis on 42 residues in the active-site region, we rapidly identified 97 previously unreported variants at 18 unique positions, significantly increasing the database of indigo-positive variants. From this expanded pool, we isolated 80 well-expressed indigo-positive variants and evaluated them alongside 46 well-expressed indigo-negative variants for their hydroxylation activity on the representative non-native aromatic compounds, anisole and naphthalene. We observed a strong correlation between indigo formation and aromatic compound hydroxylation, with 73-80% of indigo-positive variants hydroxylating these compounds, compared to 40-45% of indigo-negative variants. Notably, only indigo-positive variants showed greater than 3-fold higher activity than the wild-type P450 BM3. Furthermore, a positive correlation was obtained between promiscuous hydroxylation of anisole and naphthalene. The approach also allowed identification of new variants that hydroxylate a further aromatic compound, 4-phenyl-2-butanone, suggesting generality. Although we did not succeed in identifying the molecular basis underlying the indigo- positive phenotype, our findings demonstrate that indigo production is an effective screening tool, expediting the discovery of novel functional genes for promiscuous aromatic hydroxylation reactions. This method offers a cost-effective and efficient approach to identify and develop new biocatalysts, advancing the potential applications of P450 BM3 in scientific and industrial fields.

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 machine prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.

metaresearch head score (Codex)0.001
metaresearch head score (Gemma)0.001
Version: metacan-v3-hybrid-931329e0061cValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Simulation or modeling · Consensus signal: none
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.001
Threshold uncertainty score0.003

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0010.001
Meta-epidemiology (narrow)0.0010.000
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0010.001
Science and technology studies0.0000.000
Scholarly communication0.0010.000
Open science0.0000.000
Research integrity0.0000.001
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 head0.032
GPT teacher head0.297
Teacher spread0.265 · 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 source (direct Gemma or distilled Codex), not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designSimulation or modeling
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

Citations1
Published2024
Admission routes2
Has abstractyes

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