Evidence map›Paper›PMID 34101453›Full record

ReviewChemical reviews2021

Bioorthogonal Reactions of Triarylphosphines and Related Analogues.

Tyler K Heiss, Robert S Dorn, Jennifer A Prescher

Abstract readReview
In one paragraph

Review in Chemical reviews, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.

0numbers the graph read from it
0cells of the map it votes in
16citing 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

16 citing papers in PubMed.

  1. Review
  2. Article
  3. Article
  4. Sequence-Modulated Active Tripeptide Condensates for Tandem Catalysis.Angewandte Chemie (International ed. in English) · 2026
    Article
  5. Article
  6. Unsaturated Phosphorus Electrophiles to Probe Protein Tyrosine Phosphatases.Angewandte Chemie (International ed. in English) · 2026
    Article
  7. Article
  8. Regioselective palladium-catalysed aerobic oxidation of dextran and its use as a bio-based binder in paperboard coatings.Green chemistry : an international journal and green chemistry resource : GC · 2024
    Article
  9. Theranostic Fluorescent Probes.Chemical reviews · 2024
    Review
  10. Article
  11. Article
  12. Review
  13. Molecules (Basel, Switzerland) · 2022
    Article
  14. Article
  15. Fluorogenic Cyclopropenones for Multicomponent, Real-Time Imaging.Journal of the American Chemical Society · 2022
    Article
  16. Review
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

3 authors.

Tyler K Heiss
Jennifer A PrescherORCID 0000-0002-9250-4702

Funding

New tools for quantitative non-invasive recording of biochemical signalsR01CA279813 · NCI · UNIVERSITY OF CALIFORNIA, SAN DIEGO · PI Jennifer Prescher, Nathan Christopher Shaner · 2024 to 2026
$2.0M
Cyclopropenones to assemble, analyze, and activate biomoleculesR01GM126226 · NIGMS · UNIVERSITY OF CALIFORNIA-IRVINE · PI PRESCHER, JENNIFER · 2018 to 2021
$1.1M
NCI NIH HHS R01 CA279813NIGMS NIH HHS R01 GM126226
6 · The paper itself

Abstract

Bioorthogonal phosphines were introduced in the context of the Staudinger ligation over 20 years ago. Since that time, phosphine probes have been used in myriad applications to tag azide-functionalized biomolecules. The Staudinger ligation also paved the way for the development of other phosphorus-based chemistries, many of which are widely employed in biological experiments. Several reviews have highlighted early achievements in the design and application of bioorthogonal phosphines. This review summarizes more recent advances in the field. We discuss innovations in classic Staudinger-like transformations that have enabled new biological pursuits. We also highlight relative newcomers to the bioorthogonal stage, including the cyclopropenone-phosphine ligation and the phospha-Michael reaction. The review concludes with chemoselective reactions involving phosphite and phosphonite ligations. For each transformation, we describe the overall mechanism and scope. We also showcase efforts to fine-tune the reagents for specific functions. We further describe recent applications of the chemistries in biological settings. Collectively, these examples underscore the versatility and breadth of bioorthogonal phosphine reagents.

Indexed as

AzidesBenzene DerivativesCycloaddition ReactionPhosphinesAzidesBenzene DerivativesPhosphines

Identifiers

PMID34101453
PMCPMC10064493

What OpenQuestion holds

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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.