Glycosidase-catalyzed hydrolysis of 2-deoxyglucopyranosyl pyridinium salts: effect of the 2-OH group on binding and catalysis
Bibliographic record
Abstract
Three 2-deoxy-α-D-glucopyranosyl pyridinium tetrafluoroborates were tested for their binding affinity to a range of α-glucosidases and α-mannosidases. The α-isoquinolinium salt (11) binds approximately 275-fold more tightly to yeast α-glucosidase than does the isomeric quinolinium salt (12). In addition, compound 11 binds to the yeast enzyme approximately two-fold tighter than the corresponding glucopyranosyl isoquinolinium salt (9). The (k cat /k hyd ) values for the yeast α-glucosidase-catalyzed reactions of 11 and 9 are 1.6 × 10 5 and 2.0 × 10 9 , respectively, when compared to the spontaneous uncatalyzed reactions. Thus, the interaction of the 2-OH group in compound 9 with the yeast enzyme's active site generates a relative transition state stabilization of about 23.5 kJ mol -1 . For both compounds 11 and 12, the observed rate accelerations for the yeast α-glucosidase-catalyzed hydrolysis, relative to the spontaneous reaction in solution, (k cat /k hyd ) are identical within experimental error.Key words: glycosidase, inhibitor, 2-deoxyglucose, pyridinium, catalysis.
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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) | 0.001 | 0.001 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.003 | 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".