Evidence map›Paper›PMID 26568479›Full record

ArticleAngewandte Chemie (International ed. in English)2015

A Bioorthogonal Reaction of N-Oxide and Boron Reagents.

Justin Kim, Carolyn R Bertozzi

Abstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 27 papers.

0numbers the graph read from it
0cells of the map it votes in
27citing papers in PubMed
3.8field-weighted citation impact, top 6% of its field
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

27 citing papers in PubMed, 77 citations in OpenAlex.

  1. Review
  2. Article
  3. On-Demand Chemically Degradable Hydrogels for Biological Applications.Chembiochem : a European journal of chemical biology · 2026
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  7. EnamineSynlett : accounts and rapid communications in synthetic organic chemistry · 2024
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  11. Reductive site-selective atypicalScience advances · 2022
    Article
  12. Article
  13. Article
  14. Review
  15. EnamineACS central science · 2021
    Article
  16. Article
  17. Article
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  20. Article
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

2 authors at 2 institutions in 1 country.

Justin KimDepartment of Chemistry and Howard Hughes Medical Institute, Stanford University, 380 Roth Way, Stanford, CA 94305 (USA).
Carolyn R BertozziDepartment of Chemistry and Howard Hughes Medical Institute, Stanford University, 380 Roth Way, Stanford, CA 94305 (USA). bertozzi@stanford.edu.
Howard Hughes Medical Institute · USStanford University · US

Funding

METABOLIC OLIGOSACCHARIDE ENGINEERINGR01GM058867 · NIGMS · UNIVERSITY OF CALIFORNIA BERKELEY · PI Carolyn Bertozzi · 1999 to 2026
$5.6M
Metabolic Engineering with Bioorthogonal Chemical ReportersR37GM058867 · NIGMS · UNIVERSITY OF CALIFORNIA BERKELEY · PI BERTOZZI, CAROLYN · 2009 to 2018
$4.7M
Howard Hughes Medical InstituteNIGMS NIH HHS GM058867NIGMS NIH HHS R01 GM058867NIGMS NIH HHS R37 GM058867
6 · The paper itself

Abstract

The development of bioorthogonal reactions has classically focused on bond-forming ligation reactions. In this report, we seek to expand the functional repertoire of such transformations by introducing a new bond-cleaving reaction between N-oxide and boron reagents. The reaction features a large dynamic range of reactivity, showcasing second-order rate constants as high as 2.3×10(3)  M(-1)  s(-1) using diboron reaction partners. Diboron reagents display minimal cell toxicity at millimolar concentrations, penetrate cell membranes, and effectively reduce N-oxides inside mammalian cells. This new bioorthogonal process based on miniscule components is thus well-suited for activating molecules within cells under chemical control. Furthermore, we demonstrate that the metabolic diversity of nature enables the use of naturally occurring functional groups that display inherent biocompatibility alongside abiotic components for organism-specific applications.

Indexed as

BoronIndicators and ReagentsOxidesBoronIndicators and ReagentsOxidesbioorthogonal chemistrydiboron reagentsN-oxidessmall-molecule activationuncaging

Identifiers

PMID26568479
PMCPMC4715665
OpenAlexW2180210596

What OpenQuestion holds

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LicenceTDM
Read underepoch 390

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.