Multidimensional conformational analysis of allyl methyl disulfide: a key component of garlic
Bibliographic record
Abstract
Organosulfur compounds in garlic, like allyl methyl disulfide, have been found to be involved in antimutagenic, anticarcinogenic, antithrombotic, and lipid-lowering activities, and it has also been found to act as an antioxidant. Ab initio molecular computations were performed on dihydrogen disulfide (1) with respect to torsional angle τ 1 = τ(H·S-S·H), hydrogen methyl disulfide (2) with respect to torsional angle τ 1 = τ(H·S-S·CH 3 ), and allyl methyl disulfide (3) with respect to torsional angles τ 1 = τ(H 3 C 2 ·CH 2 ·S-S·CH 3 ), τ 2 = τ(H 3 C 2 ·CH 2 -S·S·CH 3 ), and τ 3 = τ(H 3 C 2 -CH 2 ·S·S·CH 3 ). Potential energy curves (PEC) were obtained from 1 and 2, i.e., E = E(τ 1 ), from which optimized structures were obtained at the HF/6-31G* level of theory. These optimized structures were used to investigate the potential energy hypersurface surface (PEHS) of 3, i.e., E = E(τ 1 ,τ 2 ,τ 3 ). One-dimensional scans along τ 2 and τ 3 (where τ 1 = ±90°; τ 1 = 180°) were performed at the HF/3-21G* level of theory. From these scans, six lower energy pairs of enantiomeric minima (i.e., [g + g + g + | g - g - g - ], [g + ag - | g - ag + ], [g + g - g + | g - g + g - ], [g + g + g - | g - g - g + ], [g + ag - | g - ag + ], and [g + g - g - | g - g + g + ]) as well as 3 higher energy minima (i.e., [g + g + s | g - g - s], [g + as | g - as], and [g+g - s | g - g + s]) were optimized at τ 1 = ±90° at the HF/6-31G* and B3LYP/6-31G* levels of theory. The global minimum was determined to be the [g + g - g + | g - g + g - ] enantiomeric pair of conformers, and the fully symmetrical anti-anti-anti [a a a] structure was determined to be a second-order saddle point on the PEHS of 3. Although there are no stereocentres in 3, there is chirality in the conformational twist with respect to the [a a a] conformation through τ 1 = τ 2 = τ 3 = 180°. Based on the energies and MO diagrams of the HUMO and LUMO +1 of 3, the anticarcinogenic and cholesterol lowering activity mechanism of 3 is presented.Key words: ab initio MO computations, allyl methyl disulfide, multidimensional conformational analysis (MDCA), anticarcinogenic, cholesterol lowering.
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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) | 0.006 | 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".