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Structural And Functional Analysis Of Acetylcholinesterase Complexes With “In Situ Click‐Chemistry” Inhibitors

2016· article· en· W4389023590 on OpenAlexfundno aff
P. Marchot, K. Barry Sharpless, Palmer Taylor, Yves Bourne

Bibliographic record

VenueThe FASEB Journal · 2016
Typearticle
Languageen
FieldMedicine
TopicCholinesterase and Neurodegenerative Diseases
Canadian institutionsnot available
FundersPacific Institute for Climate Solutions
KeywordsChemistryActive siteCycloadditionClick chemistryStereochemistryAcetylcholinesteraseLigand (biochemistry)AlkyneTriazoleAzideBinding siteEnzymeCombinatorial chemistryBiochemistryOrganic chemistryReceptorCatalysis

Abstract

fetched live from OpenAlex

Ligand binding sites on acetylcholinesterase (AChE) comprise the active center, buried at the base of a deep and narrow gorge lined by aromatic residues, and the peripheral anionic site, located at the gorge entry. These features propelled AChE as an initial reaction vessel suited for in situ click‐chemistry synthesis of high‐affinity syn ‐TZ2PA6 and TZ2PA5 inhibitors, forming a central syn ‐triazole upon cycloaddition within the gorge from alkyne and azide reactants bound to the active site and peripheral site, respectively [1,2]. Subsequent crystallographic analyses of mouse AChE or its Tyr337Ala mutant in complexes with the syn‐ and anti ‐TZ2PA6 regioisomers demonstrated that association of the syn product is accompanied by distinctive side chain positions, freezing‐in‐frame a conformation distinct from an unbound state or an anti complex [3,4]. To correlate the inhibitor dimensions with reactivity and explore whether cycloaddition can occur in a crystalline template, we developed crystal‐soaking procedures and solved structures of AChE complexes with the two TZ2PA5 regioisomers and their TZ2 and PA5 precursors [5]. These new structures, complementary to those of the preformed TZ2PP6 complexes, point to yet undescribed motions in the active site and at the gorge mouth associated with TZ2 binding and reveal coordinated side chain motions that guide the enzyme toward a state favoring syn ‐triazole formation. We will present the rationale of the work, describe those molecular determinants that dictate, in a rate‐limiting step, proper alignment of the azide and alkyne reactants to form the triazole product within the gorge, and compare our data with those from other in situ click chemistry studies. Support or Funding Information Supported by grants RO‐1‐GM18360‐41 and UO1‐NS 058046 (to PT) and by CNRS grants “Action CNRS/USA” and “PICS” (to PM and YB)

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 machine prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation 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 score0.002
Threshold uncertainty score0.004

Distilled classifier scores by category (both heads)

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)0.0010.000

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 head0.025
GPT teacher head0.271
Teacher spread0.246 · 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 source (direct Gemma or distilled Codex), 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".

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Citations0
Published2016
Admission routes1
Has abstractyes

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