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Record W2109574023 · doi:10.1002/ejoc.201101073

Mimicking Nature to Make Unnatural Amino Acids and Chiral Diamines

2011· article· en· W2109574023 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.
fundA Canadian funder is recorded on the work.

Bibliographic record

VenueEuropean Journal of Organic Chemistry · 2011
Typearticle
Languageen
FieldBiochemistry, Genetics and Molecular Biology
TopicChemical Synthesis and Analysis
Canadian institutionsUniversity of Toronto
FundersNatural Sciences and Engineering Research Council of Canada
KeywordsPyridoxamineChemistryTransaminationAmino acidChirality (physics)Steric effectsStereospecificityPyridoxalEnantioselective synthesisStereochemistryMoleculeEthylenediamineOrganic chemistryCatalysisChiral symmetry breakingBiochemistrySymmetry breakingEnzyme

Abstract

fetched live from OpenAlex

Abstract Biomimetic studies of pyridoxal and pyridoxamine models are of both fundamental and practical interest. This review examines (i) deracemization of α‐amino acids with a chiral pyridoxal model, (ii) sensing of chirality of small molecules including α‐, β‐, and γ‐amino acids, peptides, amino alcohols and diamines with an achiral pyridoxal model and (iii) stereospecific synthesis of chiral diamines with a chiral pyridoxamine model. A binol‐based aldehyde is useful as a chiral pyridoxal model to deracemize a variety of α‐amino acids to make D ‐amino acids. 2,2′‐Dihydroxybenzophenone is useful as an achiral pyridoxal model for sensing the chirality of the above‐mentioned small molecules in a unified way. Bis(2‐hydroxyphenyl)‐ethylenediamine ( hpen ) is useful as a chiral pyridoxamine model for making chiral diamines. Weak forces (H‐bonding, steric and electronic effects) involved in transamination reactions with pyridoxamine for the synthesis of amino acids are compared with those for the diaza‐Cope rearrangement reaction with hpen for the synthesis of chiral diamines. Both experimental and computational methods are used to analyze the biomimetic systems.

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 score0.015
Threshold uncertainty score0.543

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 head0.007
GPT teacher head0.198
Teacher spread0.191 · 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