A novel bis-phosphonyl C-glycoside: the first synthesis of C-(1,6-deoxy-β- <scp>d</scp> -glucopyranosyl)dimethylphosphonate, a stable bisphosphonate to probe the mechanism of β-phosphoglucomutase
Bibliographic record
Abstract
β-Phosphoglucomutase (β-PGM) catalyzes the interconversion of β-D-glucose-1-phosphate and β-D-glucose-6-phosphate sequentially utilizing a transient aspartyl-phospho enzyme and a β-D-glucose-1,6-bisphosphate intermediate. Herein, we report the first synthesis of the isosteric, cleavage resistant, phosphonate analogue C-(1,6-deoxy-β-D-glucopyranosyl)dimethylphosphonate, to aid in mechanistic and structural investigations of β-PGM and its phosphate transfer process. The introduction of the 'pseudo anomeric' phosphonate was accomplished through methylenephosphonate anion addition to gluconolactone, whilst the second phosphonate was installed at C-6 of the β-D-glucopyranosyl moiety using a Horner-Wadsworth-Emmons (HWE) reaction on the C-6 aldehyde. The synthesis was completed in 10 steps with 8% overall yield.
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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.
Distilled classifier scores by category (both heads)
| 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 | 0.001 |
| Insufficient payload (model declined to judge) | 0.001 | 0.001 |
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 source (direct Gemma or distilled Codex), 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".