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Record W2075394688 · doi:10.1002/ejoc.201200397

Fluorinated Carbohydrates as Lectin Ligands: Biorelevant Sensors with Capacity to Monitor Anomer Affinity in <sup>19</sup>F‐NMR‐Based Inhibitor Screening

2012· article· en· W2075394688 on OpenAlexaff
Sabine André, F. Javier Cañada, Tze Chieh Shiao, Laura Largartera, Tammo Diercks, Milan Bergeron‐Brlek, Khouzaima El Biari, Alex Papadopoulos, João P. Ribeiro, Mohamed Touaibia, Dolores Solı́s, Margarita Menéndez, Jesús Jiménez‐Barbero, René Roy, Hans‐Joachim Gabius

Bibliographic record

VenueEuropean Journal of Organic Chemistry · 2012
Typearticle
Languageen
FieldChemistry
TopicCarbohydrate Chemistry and Synthesis
Canadian institutionsUniversité de MonctonUniversité du Québec à Montréal
Fundersnot available
KeywordsChemistryAnomerLectinStereochemistryNuclear magnetic resonance spectroscopyDocking (animal)Two-dimensional nuclear magnetic resonance spectroscopyMannoseCombinatorial chemistryBiochemistry

Abstract

fetched live from OpenAlex

Abstract Our recent description of pulse sequences for the intramolecular relay of 1 H polarization to the 19 F reporter of a carbohydrate ligand after saturation transfer from a cognate lectin prompted us to test the applicability of this technique for inhibitor screening. By strategically combining synthetic organic chemistry and cell assays with 19 F‐NMR‐based competition experiments, we document the validity of this approach. Two mannose‐specific leguminous agglutinins as receptors, the α‐methyl derivative of 2‐deoxy‐2‐fluoro‐ D ‐mannopyranoside as sensor and synthetic mannosides selected to represent different inhibitory capacities were used to establish a test panel. Signal amplitudes were found to vary among the two related lectins, and their precipitation by glycodendrimers enabled inherent limits to be set. The obtained experimental basis was then broadened by assaying a galactopyranoside‐binding plant toxin, using 6‐deoxy‐6‐fluoro‐ D ‐galactopyranose as a sensor molecule. The easy identification of the two anomeric signals by 19 F NMR spectroscopy enabled ready detection of the preference of this lectin for the α‐anomer and allowed the two individual inhibition profiles to be deduced. These 19 F NMR spectroscopic data were in accord with the activities of inhibitors used to protect cells from toxicity. Our results therefore provide an experimental basis for 19 F‐NMR‐based inhibitor screening.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame distilled prediction

Teacher imitation

Not 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.

metaresearch head score (Codex)0.001
metaresearch head score (Gemma)0.001
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow), Insufficient payload (model declined to judge)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.007
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.001
Meta-epidemiology (narrow)0.0010.001
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0000.001
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0020.000

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.

Opus teacher head0.017
GPT teacher head0.214
Teacher spread0.198 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one teacher head, not a consensus.

Study designBench or experimental
Domainnot available
GenreEmpirical

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".

Quick stats

Citations21
Published2012
Admission routes1
Has abstractyes

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