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Record W2318915536 · doi:10.1021/ct100450s

Theoretical Investigations on the Conformation of the β-<scp>d</scp>-Arabinofuranoside Ring

2010· article· en· W2318915536 on OpenAlexaff
Hashem A. Taha, Pierre–Nicholas Roy, Todd L. Lowary

Bibliographic record

VenueJournal of Chemical Theory and Computation · 2010
Typearticle
Languageen
FieldChemistry
TopicCarbohydrate Chemistry and Synthesis
Canadian institutionsAlberta Glycomics CentreUniversity of AlbertaUniversity of Waterloo
Fundersnot available
KeywordsRing (chemistry)ChemistryStereochemistryComputer scienceComputational biologyBiologyOrganic chemistry

Abstract

fetched live from OpenAlex

A method for the conformational analysis of furanose rings that involves the prediction of (3)JH,H that can be compared directly to experimental values is investigated. This method, which differs from the traditional PSEUROT approach for conformational studies of furanose rings, was previously applied to a number of α-d-arabinofuranosides and enabled the direct comparison of (3)JH,H values to those obtained from NMR spectroscopy. In this paper, the use of this approach to study the conformational preferences of oligosaccharides containing β-linked arabinofuranose residues is reported. Density functional theory (DFT) calculations were carried out to derive Karplus relationships that are specifically tailored for these ring systems. In addition, probability distributions obtained from GLYCAM/AMBER molecular dynamics simulations were employed to calculate (3)JH,H values from these Karplus relationships. However, unlike the results obtained with α-arabinofuranosides, the (3)JH,H values computed for β-arabinofuranosides agreed poorly with experimental values. This prompted the exploration of other methodologies including reevaluation and optimization of the initial MD protocol, use of various force field models, and recalculation of the DFT-derived coupling profiles using an optimized basis set. After extensive investigations, we established that the conformer distributions obtained from MD simulations with the GLYCAM force fields and the furanoside-specific CHARMM force field in combination with the DFT Karplus equations, determined using an augmented basis set (B3LYP/aug-cc-pVTZ-J), produced the best agreement compared to experimental (3)JH,H values. Using these protocols, there is relatively good agreement in (3)JH,H for all coupling pathways with the exception of (3)J2,3 and (3)J3,4, which are underestimated.

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)0.002
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesnone
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 score0.013
Threshold uncertainty score0.266

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.002
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.001
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0000.000

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 head0.009
GPT teacher head0.223
Teacher spread0.213 · 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.

The models applied no category: nothing in the taxonomy fit this work.
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

Citations23
Published2010
Admission routes1
Has abstractyes

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