The Light-induced Reactions of Tryptophan with Halocompounds¶
Bibliographic record
Abstract
The light-dependent reaction between N-acetyl-L-tryptophanamide (NATA) and chloroform has been examined using fluorescence, NMR and reverse phase chromatography. The emission of NATA in the presence of CHCl3 decreases at 360 nm and increases at longer wavelengths (approximately 480 nm) upon illumination with 280 nm light. The action spectrum for the formation of the 480 nm emitting product(s) has the same shape as the excitation spectra of the indole fluorophore in NATA. The pH of the solution decreases as the reaction proceeds. The reaction rate depends on the intensity of the illumination and is of the first order with respect to both [NATA] and [CHCl3]. NMR and reverse phase chromatography results demonstrate that multiple products are formed. The reaction products give new peaks between 8.9 and 10.5 ppm in the 1H-NMR that are assigned to -CHO groups, which are added to the indole ring. Some of the products react with 2,4-dinitrophenylhydrazine and thus confirm this assignment. A scheme is proposed in which the excited indole gives off a solvated electron to initiate a series of steps that yield indole derivatives in which a -CHO group has replaced a -H in the indole ring. Similar reactions are observed when 5-hydroxytryptophan, 5-fluorotryptophan or N-methylindolacetate is used instead of tryptophan or when the chloroform is replaced with other trichlorinated compounds, such as trichloroacetic acid, trichloroethanol and trichloroethane, as well as the tribrominated compound, bromoform, and the monoiodinated compound, iodoactetate.
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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) | 0.001 | 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".