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Record W4234506686 · doi:10.26434/chemrxiv.11933232.v1

Thioesterase from Cereulide Biosynthesis Is Responsible for Oligomerization and Macrocyclization of a Linear Tetradepsipeptide

2020· preprint· en· W4234506686 on OpenAlexaff
Christopher N. Boddy, Graham W. Heberlig

Bibliographic record

VenueChemRxiv · 2020
Typepreprint
Languageen
FieldBiochemistry, Genetics and Molecular Biology
TopicChemical Synthesis and Analysis
Canadian institutionsUniversity of Ottawa
Fundersnot available
KeywordsValinomycinThioesteraseBiosynthesisChemistryStereochemistrySubstrate (aquarium)BiochemistryBiologyEnzyme

Abstract

fetched live from OpenAlex

Cereulide is a cyclic depsidodecapeptide produced in Bacillus cereus by two non-ribosomal peptide synthetases, CesA and CesB. While highly similar in structure and with a homologous biosynthetic gene cluster to valinomycin, recent work suggests that cereulide is produced via a different mechanism, which relys on a non-canonical coupling of two didepsipeptide-PCP bound intermediates. Ultimately this alternative mechanism generates a tetradepsipeptide-PCP bound intermediate that is prosed to differ from the tetradepsipeptide predicted from canonical activity of CesA and CesB. To test this hypothesis, we chemically synthetize both tetradepsipeptides as N-acetyl cysteamine thioesters and probed the ability of the purified recombinant terminal CesB thioesterase (CesB TE) to oligomerize and macrocyclize each substrate. Only the canonical substrate is converted cereulide, ruling out this alternative mechanism. We also show that CesB TE can use related tertradepsipeptide substrates, such as the valinomycin tetradespipetide and a hybride cereulide-valinomycin tetradespispetide in conjunction with its native substrate to generate chimeric natural products. This work clarifies the biosynthetic origins of cereulide and provides a powerful biocatalyst to access analogs of these ionophoric forming natural products.

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)0.000
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation 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 score0.001
Threshold uncertainty score0.003

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0010.000
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)0.0010.001

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 head0.022
GPT teacher head0.268
Teacher spread0.246 · 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 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

Citations0
Published2020
Admission routes1
Has abstractyes

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