Evidence map›Paper›PMID 33730425›Full record

ArticleAngewandte Chemie (International ed. in English)2021

Oligonucleotide Bioconjugation with Bifunctional Palladium Reagents.

Muhammad Jbara, Jacob Rodriguez, Heemal H Dhanjee, Andrei Loas, Stephen L Buchwald, Bradley L Pentelute

Abstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 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. Review
  3. Review
  4. Article
  5. Article
  6. Review
  7. Article
  8. Article
  9. Ultrafast Au(III)-Mediated Arylation of Cysteine.Journal of the American Chemical Society · 2024
    Article
  10. Article
  11. Recent Advances in Bioorthogonal Ligation and Bioconjugation.Topics in current chemistry (Cham) · 2023
    Review
  12. Article
  13. Review
  14. Pd(II)-Mediated C-H Activation for Cysteine Bioconjugation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022
    Article
  15. Review
  16. 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.

Muhammad JbaraDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, MA, 02139, USA.ORCID 0000-0002-4206-5908
Jacob RodriguezDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, MA, 02139, USA.
Heemal H DhanjeeDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, MA, 02139, USA.
Andrei LoasDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, MA, 02139, USA.
Stephen L BuchwaldDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, MA, 02139, USA.
Bradley L PenteluteDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, MA, 02139, USA.ORCID 0000-0002-7242-801X

Funding

TOXICOLOGY CORE UNITP30ES002109 · NIEHS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI FOX, JAMES G · 1985 to 2020
$25.6M
Chemo- and Regio- Selective Lysine Modification on the Surface of Native Proteins: Synthetic Methods for the Improvement of Cancer TherapeuticsF32GM131592 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI DHANJEE, HEEMAL · 2019 to 2022
$145k
NIEHS NIH HHS P30 ES002109NIGMS NIH HHS F32 GM131592
6 · The paper itself

Abstract

Organometallic reagents enable practical strategies for bioconjugation. Innovations in the design of water-soluble ligands and the enhancement of reaction rates have allowed for chemoselective cross-coupling reactions of peptides and proteins to be carried out in water. There are currently no organometallic-based methods for oligonucleotide bioconjugation to other biomolecules. Here we report bifunctional palladium(II)-oxidative addition complexes (OACs) as reagents for high-yielding oligonucleotide bioconjugation reactions. These bifunctional OACs react chemoselectively with amine-modified oligonucleotides to generate the first isolable, bench stable oligonucleotide-palladium(II) OACs. These complexes undergo site-selective C-S arylation with a broad range of native thiol-containing biomolecules at low micromolar concentrations in under one hour. This approach provided oligonucleotide-peptide, oligonucleotide-protein, oligonucleotide-small molecule, and oligonucleotide-oligonucleotide conjugates in >80 % yield and afforded conjugation of multiple copies of oligonucleotides onto a monoclonal antibody.

Indexed as

Cross-Linking ReagentsOligonucleotidesOrganometallic CompoundsPalladiumPeptidesTrastuzumabCross-Linking ReagentsOligonucleotidesOrganometallic CompoundsPalladiumPeptidesTrastuzumabbioconjugationoligonucleotidesorganometallic reagentspalladium oxidative addition complexesproteins

Identifiers

PMID33730425
PMCPMC8143041

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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.