Dual use of a chemical auxiliary: molecularly imprinted polymers for the selective recovery of products from biocatalytic reaction mixtures
Bibliographic record
Abstract
Auxiliary-directed biocatalysis is a powerful and relatively benign tool for chemical synthesis. We recently reported the use of theobromine as a chemical auxiliary for directing CYP3A4-catalyzed oxidations with predictable regio-, chemo- and stereo-selectivity (J. Am. Chem. Soc., 2011, 133, 7853). This highly successful strategy enabled the direct, regio- and stereo-selective hydroxylation of unactivated C–H bonds. However, recovering the products and starting materials from the resulting biocatalytic mixtures has proven challenging. To address this issue, we capitalized on the chemical auxiliary present on the starting material and enzymatic reaction products. The chemical auxiliary was used as a template to generate molecularly imprinted polymers (MIPs). When used in solid-phase extractions, the MIPs reported here allow for the recovery (>90%) of theobromine-containing products and starting materials from complex mixtures such as cellular membrane extracts. This strategy, which avoids the use of large amounts of organic solvents, represents an effective, easily-tailored, and reusable way to improve the recovered yield of biocatalytic transformations while extending the usefulness of a chemical auxiliary.
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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot 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.
Distilled classifier scores by category (both heads)
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.001 | 0.001 |
| Meta-epidemiology (narrow) | 0.001 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.001 |
| Open science | 0.001 | 0.001 |
| Research integrity | 0.001 | 0.001 |
| Insufficient payload (model declined to judge) | 0.001 | 0.001 |
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.
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 source (direct Gemma or distilled Codex), 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".