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Record W4287835474 · doi:10.1002/open.202200119

Application of 2D EXSY and qNMR Spectroscopy for Diastereomeric Excess Determination Following Chiral Resolution of β‐Lactams

2022· article· en· W4287835474 on OpenAlex

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.

Bibliographic record

VenueChemistryOpen · 2022
Typearticle
Languageen
FieldChemistry
TopicAnalytical Chemistry and Chromatography
Canadian institutionsTrinity College
FundersScience Foundation IrelandTrinity College DublinWellcome Trust
KeywordsDiastereomerEnantiopure drugChemistryConformational isomerismStereochemistryResolution (logic)Nuclear magnetic resonance spectroscopyTwo-dimensional nuclear magnetic resonance spectroscopyChiral resolutionLactamCombinatorial chemistryOrganic chemistryEnantiomerMoleculeEnantioselective synthesisCatalysis

Abstract

fetched live from OpenAlex

Abstract Trans‐ β‐lactam isomers have garnered much attention as anti‐cancer microtubule targeting agents. Currently available synthetic methods are available for the preparation of enantiopure β‐lactams and favour isomeric cis/trans β‐lactam mixtures. Indirect chiral resolution offers the opportunity for isolation of exclusively enantiopure trans‐ β‐lactams. In this study, liquid chromatography chiral resolution of β‐lactams derivatized as diastereomer mixtures with a panel of N ‐protected amino acids is explored, where N‐( Boc)‐L‐proline served as the optimal chiral derivatising reagent. High‐performance liquid chromatography failed to adequately determine diastereomeric excess ( de ) of resolved diastereomers. Variable temperature, 1 H NMR and 2D EXSY spectroscopic analyses of proline‐derivatised diastereomers were successfully employed to characterise equilibrating rotamers of resolved diastereomers and determine their de . Integration of resolved resonances corresponding to H 3 and H 4 of the β‐lactam ring served as a quantitative qNMR tool for the calculation of de following resolution.

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.

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)0.000
metaresearch head score (Gemma)0.000
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 score0.011
Threshold uncertainty score0.681

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
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 head0.259
Teacher spread0.250 · 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