Evidence map›Paper›PMID 33085477›Full record

ArticleJournal of the American Chemical Society2020

Triple, Mutually Orthogonal Bioorthogonal Pairs through the Design of Electronically Activated Sulfamate-Containing Cycloalkynes.

Yun Hu, Jessica M Roberts, Henry R Kilgore, Amirah S Mat Lani, Ronald T Raines, Jennifer M Schomaker

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.

0numbers the graph read from it
0cells of the map it votes in
17citing 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

17 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Review
  5. Review
  6. Article
  7. Glutathione Mediates Control of Dual Differential Bio-orthogonal Labelling of Biomolecules.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2023
    Article
  8. Article
  9. Review
  10. Article
  11. Review
  12. SuFExableThe Journal of organic chemistry · 2022
    Article
  13. Photoinduced movement: how photoirradiation induced the movements of matter.Science and technology of advanced materials · 2022
    Review
  14. Review
  15. Bioorthogonal Hydroamination of Push-Pull-Activated Linear Alkynes.Angewandte Chemie (International ed. in English) · 2021
    Article
  16. Article
  17. Bioorthogonal Retro-Cope Elimination Reaction ofJournal of the American Chemical Society · 2021
    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

6 authors.

Yun HuDepartment of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States.ORCID 0000-0002-0385-3362
Jessica M RobertsDepartment of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States.
Henry R KilgoreDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.ORCID 0000-0003-4851-9656
Amirah S Mat LaniDepartment of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States.
Ronald T RainesDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.ORCID 0000-0001-7164-1719
Jennifer M SchomakerDepartment of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States.ORCID 0000-0003-1329-950X

Funding

STRUCTURE--FUNCTION ANALYSIS OF RIBONUCLEASE AR01GM044783 · NIGMS · UNIVERSITY OF WISCONSIN-MADISON · PI RAINES, RONALD T · 1990 to 2021
$7.1M
Laser-Enhanced NMR Instrumentation for Chemical and Biochemical ResearchS10OD012245 · OD · UNIVERSITY OF WISCONSIN-MADISON · PI CAVAGNERO, SILVIA · 2013 to 2013
$1.0M
QExactive (Orbitrap) mass spectrometerS10OD020022 · OD · UNIVERSITY OF WISCONSIN-MADISON · PI VESTLING, MARTHA M · 2015 to 2015
$483k
NIGMS NIH HHS R01 GM044783NIH HHS S10 OD012245NIH HHS S10 OD020022
6 · The paper itself

Abstract

Interest in mutually exclusive pairs of bioorthogonal labeling reagents continues to drive the design of new compounds that are capable of fast and predictable reactions. The ability to easily modify S-, N-, and O-containing cyclooctynes (SNO-OCTs) enables electronic tuning of various SNO-OCTs to influence their cycloaddition rates with Type I-III dipoles. As opposed to optimizations based on just one specific dipole class, the electrophilicity of the alkynes in SNO-OCTs can be manipulated to achieve divergent reactivities and furnish mutually orthogonal dual ligation systems. Significant reaction rate enhancements of a difluorinated SNO-OCT derivative, as compared to the parent scaffold, were noted, with the second-order rate constant in cycloadditions with diazoacetamides exceeding 5.13 M

Indexed as

AnimalsCHO CellsCricetinaeCricetulusCycloaddition ReactionCycloparaffinsFluorescent DyesMicroscopy, FluorescenceMolecular ConformationNitrogenOxygenSulfonic AcidsSulfurThermodynamicsCycloparaffinsFluorescent DyesNitrogenOxygensulfamic acidSulfonic AcidsSulfur

Identifiers

PMID33085477
PMCPMC7891878

What OpenQuestion holds

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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.