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Record W2897679657 · doi:10.1002/chem.201804662

New Irreversible α‐<scp>l</scp>‐Iduronidase Inhibitors and Activity‐Based Probes

2018· article· en· W2897679657 on OpenAlexaff
Marta Artola, C.J. Kuo, S.A. McMahon, Verena Oehler, Thomas Hansen, Martijn J. C. van der Lienden, Xu He, Hans van den Elst, Bogdan I. Florea, Allison R. Kermode, Gijsbert A. van der Marel, T.M. Gloster, Jeroen D. C. Codée, Herman S. Overkleeft, Johannes M. F. G. Aerts

Bibliographic record

VenueChemistry - A European Journal · 2018
Typearticle
Languageen
FieldChemistry
TopicCarbohydrate Chemistry and Synthesis
Canadian institutionsSimon Fraser University
FundersH2020 European Research CouncilGenzymeNederlandse Organisatie voor Wetenschappelijk OnderzoekWellcome TrustDiamond Light SourceSanofi
KeywordsCovalent bondChemistryEnzymeStereochemistryBiochemistryOrganic chemistry

Abstract

fetched live from OpenAlex

Abstract Cyclophellitol aziridines are potent irreversible inhibitors of retaining glycosidases and versatile intermediates in the synthesis of activity‐based glycosidase probes (ABPs). Direct 3‐amino‐2‐(trifluoromethyl)quinazolin‐4(3 H )‐one‐mediated aziridination of l ‐ ido ‐configured cyclohexene has enabled the synthesis of new covalent inhibitors and ABPs of α‐ l ‐iduronidase, deficiency of which underlies the lysosomal storage disorder mucopolysaccharidosis type I (MPS I). The iduronidase ABPs react covalently and irreversibly in an activity‐based manner with human recombinant α‐ l ‐iduronidase (rIDUA, Aldurazyme ® ). The structures of IDUA when complexed with the inhibitors in a non‐covalent transition state mimicking form and a covalent enzyme‐bound form provide insights into its conformational itinerary. Inhibitors 1 – 3 adopt a half‐chair conformation in solution ( 4 H 3 and 3 H 4 ), as predicted by DFT calculations, which is different from the conformation of the Michaelis complex observed by crystallographic studies. Consequently, 1 – 3 may need to overcome an energy barrier in order to switch from the 4 H 3 conformation to the transition state ( 2, 5 B) binding conformation before reacting and adopting a covalent 5 S 1 conformation. rIDUA can be labeled with fluorescent Cy5 ABP 2 , which allows monitoring of the delivery of therapeutic recombinant enzyme to lysosomes, as is intended in enzyme replacement therapy for the treatment of MPS I patients.

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)0.000
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 score0.089
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.001
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 science0.0010.000
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 head0.014
GPT teacher head0.210
Teacher spread0.196 · 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

Citations17
Published2018
Admission routes1
Has abstractyes

Explore more

Same venueChemistry - A European JournalSame topicCarbohydrate Chemistry and SynthesisFrench-language works237,207