Evidence map›Paper›PMID 40560157›Full record

ArticleChemistry (Weinheim an der Bergstrasse, Germany)2025

Double-Click Strategy Combining CuAAC and (Thia-) Diels-Alder Reactions; Application Toward Peptide Labeling.

Timothé Maujean, Camille Van Wesemael, Laurine Tual, Valentine Le Berruyer, Blanca Rodriguez-Noguer, Nicolas Girard, Dominique Bonnet, Mihaela Gulea

Abstract read
In one paragraph

Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

0numbers the graph read from it
0cells of the map it votes in
0citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

0 citing papers in PubMed.

No citing paper in PubMed yet.

4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

8 authors.

Timothé MaujeanLaboratoire d'Innovation Thérapeutique, Université de Strasbourg, CNRS, LIT UMR 7200F, Strasbourg, 67000, France.ORCID https://orcid.org/0000-0002-8268-608X
Camille Van WesemaelLaboratoire d'Innovation Thérapeutique, Université de Strasbourg, CNRS, LIT UMR 7200F, Strasbourg, 67000, France.ORCID https://orcid.org/0000-0002-1813-5806
Laurine TualLaboratoire d'Innovation Thérapeutique, Université de Strasbourg, CNRS, LIT UMR 7200F, Strasbourg, 67000, France.
Valentine Le BerruyerLaboratoire d'Innovation Thérapeutique, Université de Strasbourg, CNRS, LIT UMR 7200F, Strasbourg, 67000, France.ORCID https://orcid.org/0009-0009-9079-1670
Blanca Rodriguez-NoguerLaboratoire d'Innovation Thérapeutique, Université de Strasbourg, CNRS, LIT UMR 7200F, Strasbourg, 67000, France.
Nicolas GirardLaboratoire d'Innovation Thérapeutique, Université de Strasbourg, CNRS, LIT UMR 7200F, Strasbourg, 67000, France.ORCID https://orcid.org/0000-0003-4610-9872
Dominique BonnetLaboratoire d'Innovation Thérapeutique, Université de Strasbourg, CNRS, LIT UMR 7200F, Strasbourg, 67000, France.ORCID https://orcid.org/0000-0002-8252-9199
Mihaela GuleaLaboratoire d'Innovation Thérapeutique, Université de Strasbourg, CNRS, LIT UMR 7200F, Strasbourg, 67000, France.ORCID https://orcid.org/0000-0002-2945-0078

Funding

IdEx Unistra ANR-10-IDEX-0002SFRI-STRAT'US ANR-20-SFRI- 0012
6 · The paper itself

Abstract

We report an efficient double-click strategy combining copper-catalyzed azide-alkyne cycloaddition (CuAAC) with (thia-)Diels-Alder (DA) reactions, enabled by newly designed heterobifunctional platforms bearing orthogonal clickable groups: alkyne-dithioester, alkyne-maleimide, or azide-diene. These platforms were evaluated through both one-pot sequential protocols (CuAAC/DA or CuAAC/thia-DA) and three-component reactions (3CR), using model substrates with complementary functionalities. The use of a highly reactive s-cis-constrained exocyclic diene, enabled rapid cycloadditions with maleimide or phosphonodithioester dienophiles. All reactions were performed under mild, biocompatible conditions (37 °C, 1:1 H₂O/iPrOH, 1-2 hours), and most afforded the desired conjugates in good isolated yields. The methodology was further validated through the successful bioconjugation of three small peptides with either a fluorophore or biotin, demonstrating its efficiency, versatility, and compatibility with biologically relevant functional groups.

Indexed as

AlkynesAzidesCopperPeptidesBiotinCatalysisClick ChemistryCycloaddition ReactionMaleimidesAlkynesAzidesBiotinCoppermaleimideMaleimidesPeptidescuaacdiels‐alder reactiondithioesterdouble‐click strategypeptide labeling

Identifiers

PMID40560157
PMCPMC12284613

What OpenQuestion holds

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LicenceCC BY-NC
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Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.