Chemical diversification of polyprenyl quinones for mechanistic studies on menaquinone-binding peptide antibiotics
Bibliographic record
Abstract
Polyprenyl quinones, such as ubiquinone and menaquinone, are essential membrane-embedded redox cofactors that are involved in electron transport and found across all domains of life. However, their highly hydrophobic structure, which includes a quinone head-group and long polyprenyl tail, has limited their chemical derivatization for biological studies. Here, we report a versatile synthetic approach for the chemical diversification of natural polyprenyl quinones, enabling the introduction of various reporter groups including fluorophores, quenchers, NMR-active nuclei, and photoaffinity and bioaffinity tags. These functionalized analogues retain their membrane-associating properties and enable new applications in antibiotic discovery. We show that fluorescently labelled menaquinone analogues retain their strong binding affinity to the menaquinone-binding peptide antibiotics lysocin E and lysomeb (MBA2). Incorporation of BODIPY-quinones into vesicles allowed visualization of the peptide-quinone interaction, revealing their effects on membrane integrity and quinone aggregation. This study expands the chemical toolbox for polyprenyl quinones, enabling targeted functionalization of these essential biomolecules and facilitating further exploration of their roles in biological systems.
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How this classification was reachedexpand
Full frame distilled prediction
Teacher imitationNot 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.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.001 | 0.001 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.001 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.000 | 0.000 |
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.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from itClassification
machine, unvalidatedMachine predicted; a candidate call from one teacher head, not a consensus.
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".