Sialoside clusters as potential ligands for siglecs (sialoadhesins)
Bibliographic record
Abstract
Clusters of O- and S-linked α-sialosides with valencies of two to four were constructed to serve as potential multivalent inhibitors towards sialoadhesins (siglecs). Thus, O- and S-prop-2-ynyl α-sialosides (3, 7), together with 4-iodophenyl sialoside 5 were prepared from acetochloroneuraminic acid derivative 1 using silver salicylate and propargyl alcohol for 3 and phase-transfer catalysis for 5 and 7, respectively. Oxidative acetylenic homocoupling of 3 and 7 under Glaser conditions (CuCl, O 2 ) provided 1,3-diynes 8 and 9 in 83-86% yields. Palladium catalyzed cross-coupling of O-prop-2-ynyl sialoside 3 with 5 using Pd 2 (dba) 3 and PPh 3 gave nonsymmetrical dimer 10 (82%). Alternatively, symmetrical clusters were then prepared as above under Sonogashira cross-coupling conditions with 1,4-diiodobenzene (11), 1,3,5-triodobenzene (14), and finally 1,2,4,6-tetraiodobenzene (17) to provide both O- and S-linked dimers 12 (93%) and 13 (88%), trimers 15 (81%) and 16 (76%), while only O-linked tetramer 18 was prepared in 87% yield. Finally, treatment of the O-linked prop-2-ynyl sialoside 3 with Grubbs' metathesis catalyst Cl 2 Ru(PCy 3 ) 2 =CHPh (19) gave, as expected, benzeneannulation regioisomeric trimers 20a, 20b in 68% yield.Key words: siglec, sialoadhesins, sialic acid, Sonogashira, palladium cross-coupling.
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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 | 0.001 |
| 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 | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.009 | 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".