Evidence map›Paper›PMID 29754834›Full record

ArticleBioorganic & medicinal chemistry2018

Site-specific incorporation of quadricyclane into a protein and photocleavage of the quadricyclane ligation adduct.

Frederick M Tomlin, Chelsea G Gordon, Yisu Han, Taia S Wu, Ellen M Sletten, Carolyn R Bertozzi

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Bioorganic & medicinal chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.

0numbers the graph read from it
0cells of the map it votes in
3citing 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

3 citing papers in PubMed.

  1. Review
  2. Article
  3. 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

6 authors.

Frederick M TomlinDepartment of Chemistry, Stanford University, Stanford, CA 94305, United States; Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720, United States.
Chelsea G GordonDepartment of Chemistry, University of California, Berkeley, Berkeley, CA 94720, United States.
Yisu HanDepartment of Chemistry, University of California, Berkeley, Berkeley, CA 94720, United States.
Taia S WuDepartment of Chemistry, Stanford University, Stanford, CA 94305, United States.
Ellen M SlettenDepartment of Chemistry, University of California, Berkeley, Berkeley, CA 94720, United States.
Carolyn R BertozziDepartment of Chemistry, Stanford University, Stanford, CA 94305, United States; Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720, United States; Howard Hughes Medical Institute, Stanford University, Stanford, CA 94305, United States. Electronic address: bertozzi@stanford.edu.

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 R01 GM058867NIGMS NIH HHS R37 GM058867
6 · The paper itself

Abstract

The quadricyclane (QC) ligation is a bioorthogonal reaction between a quadricyclane moiety and a nickel bis(dithiolene) derivative. Here we show that a QC amino acid can be incorporated into a protein site-specifically using the pyrrolysine-based genetic code expansion platform, and subsequently used for ligation chemistry. Additionally, we exploited the photolability of the QC ligation product to render the adduct cleavable with a handheld UV lamp. We further developed a protein purification method that involves QC ligation of biotin to a protein of interest, capture on streptavidin resin, and finally release using only UV light. The QC ligation thus brings novel chemical manipulations to the realm of bioorthogonal chemistry.

Indexed as

Ultraviolet RaysBiotinBridged-Ring CompoundsCoordination ComplexesLysineNickelPhotolysisStreptavidinBiotinBridged-Ring CompoundsCoordination ComplexesLysineNickelpyrrolysinequadricyclaneStreptavidinBioorthogonalPhotocleavagePhotolysisProtein purificationPyrrolysineQuadricyclaneUnnatural amino acid

Identifiers

PMID29754834
PMCPMC6170726

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.