Design and synthesis of selenonium and sulfonium ions related to the naturally occurring glucosidase inhibitor salacinol
Bibliographic record
Abstract
Four series of analogues of the naturally occurring glucosidase inhibitor salacinol were synthesized for structure–activity studies with different glycosidase enzymes. The target zwitterionic compounds were synthesized by means of nucleophilic attack at the least-hindered carbon atom of the 1,3-cyclic sulfates derived from D-glucose and D-mannose by the isopropylidene-protected 1,4-anhydro-4-thio- and seleno-D-allitols and the 4-thio- and seleno-L-allitols. Deprotection of the coupled products afforded the novel sulfonium and selenonium ions containing polyhy droxylated acyclic chains of four and six carbons, with different stereochemistry at the stereogenic centers and with 1,4-anhydro-4-seleno or 4-thio-D- or L- alditol heterocyclic rings. The compounds showed no significant activity against recombinant human maltase glucoamylase (MGA), a critical intestinal glucosidase involved in the processing of oligosaccharides of glucose into glucose itself.Key words: glycosidase inhibitors, zwitterionic, selenonium salts, sulfonium salts, cyclic sulfates, L-ascorbic acid, D-gulonic-γ-lactone.
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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".