Galactosylated 5‐Hydroxylysine Mimetics for Glycopeptide Synthesis
Bibliographic record
Abstract
Abstract The design and synthesis of four galactosylated 5‐hydroxylysine mimetic building blocks ( 2 − 5 ), conveniently protected for solid‐phase glycopeptide synthesis, is described. Our approach features: i ) a short and divergent route to the corresponding protected amino acid aglycons 6 − 9 that involves selective ring‐opening of enantiopure 5‐hydroxylated 6‐oxo‐1,2‐piperidinedicarboxylate 10 and 11 with sodium borohydride in ethanol with formation of the corresponding 1,2‐diol; ii ) a common δ‐lactam precursor 12 , readily accessible from Boc‐Asp‐O t Bu (3 steps, 74% yield), that can be hydroxylated with a high level of asymmetric induction; iii ) the use of tetra‐pivaloylated galactosyl bromide as galactosyl donor to avoid or limit orthoester formation. The four galactosylated hydroxylysine analogues 2 − 5 are suitable building blocks for incorporation into immunodominant peptides derived from type II collagen (CII) and for future investigations aimed at determining the fine specificity of arthritogenic T‐cells in collagen‐induced arthritis (CIA), a mouse model for rheumatoid arthritis (RA). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
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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 | 0.001 | 0.002 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 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) | 0.005 | 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".