Lipase-Catalyzed Michael Addition in ‘Water-like’ Ionic Liquids and Tertiary Amides: What Is the Role of the Enzymes?
Bibliographic record
Abstract
Michael addition is an important reaction to form C–C bonds. Different hydrolases (e.g., lipases, proteases, and d -aminoacylase) have been reported to catalyze C–C-forming reactions, but the reaction mechanism is not entirely clear. This study examined several model Michael reactions catalyzed by lipases and amino acids in various solvents and found that “water-like” functionalized ionic liquids (ILs) increased the reaction yield to 35–55% from 30% in triglyme and 17% in [BMIM][Tf 2 N]. Interestingly, tertiary amides as solvents remarkably increased the reaction yield (to up to 65–85%) and enantioselectivity (up to 71–84% ee ) when catalyzed by porcine pancreatic lipase (PPL). Our experimental, spectroscopic, and computational studies discovered that the lipase catalysis can be attributed to basic amino acid residues as the catalysts to promote Michael addition, especially when tertiary amide solvents partially unfold the protein and expose its (basic) amino acid residues.
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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 | 0.000 | 0.000 |
| 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 | 0.000 |
| 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".