First separation of commendamide enantiomers
Bibliographic record
Abstract
N-(3-hydroxyacyl)glycines are compounds of remarkable interest due to their biogenic origin and bioactivity and as precursors of the corresponding 3-acyloxy derivatives which represent an important class of bioactive products of bacterial origin. Commendamide [N-(3-hydroxypalmitoyl)glycine] (1) is a gut microbiota-derived bioactive metabolite that is structurally like endogenous long-chain N-acyl-amino acids belonging to the endocannabinoidome, a complex lipid signaling system involved in several aspects of mammalian physiology and pathology. Thanks to this structural similarity, this compound and its analogues, like the N-(3-hydroxymyristoyl)glycine 2, exert a remarkable bioactivity in mammals, for instance, through activation of G-protein-coupled receptors (GPCRs). N-(3-Hydroxyacyl)glycines are chiral and the availability of their pure enantiomers may bring light to possible enantioselective pathways within the biological processes which these compounds are involved in. A sustainable synthesis of rac-1 and its analogues was recently reported, but asymmetric synthesis and enantioseparation methods to access their pure or enriched enantiomers were not reported so far. In this paper, we report the first direct separation of commendamide enantiomers by using enantioselective high-performance liquid chromatography (HPLC) with polysaccharide-based chiral columns, aqueous-organic mixtures as mobile phases and either electrospray ionization mass spectrometry (ESI-MS) or UV detection. Optimal enantioseparation was obtained by using an amylose tris(3,5-dimethylphenylcarbamate)-based chiral column and acetonitrile/water 60:40 (v/v) (0.1 % acetic acid) as mobile phase. By adopting the same method, the enantioseparation of the analogue 2 was also performed. The molecular bases of the higher retention and selectivity observed for the N-(3-hydroxyacyl)glycine 1 compared to the analogue 2 were explored by computational analysis.
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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 | 0.001 |
| Bibliometrics | 0.000 | 0.001 |
| 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) | 0.003 | 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".