Evidence map›Paper›PMID 32364380›Full record

ArticleJournal of the American Chemical Society2020

Protein-Protein Cross-Coupling via Palladium-Protein Oxidative Addition Complexes from Cysteine Residues.

Heemal H Dhanjee, Azin Saebi, Ivan Buslov, Alexander R Loftis, Stephen L Buchwald, Bradley L Pentelute

Erratum issuedAbstract 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. An erratum has been issued. Cited by 25 papers.

0numbers the graph read from it
0cells of the map it votes in
25citing 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

25 citing papers in PubMed.

  1. Article
  2. Article
  3. One-Step Maleimide-Based Dual Functionalization of Protein N-Termini.Angewandte Chemie (International ed. in English) · 2025
    Article
  4. Article
  5. Review
  6. Article
  7. Article
  8. Article
  9. Recent Advances in Bioorthogonal Ligation and Bioconjugation.Topics in current chemistry (Cham) · 2023
    Review
  10. Review
  11. Article
  12. Review
  13. Article
  14. Platform for OrthogonalJournal of the American Chemical Society · 2022
    Article
  15. Article
  16. Pd(II)-Mediated C-H Activation for Cysteine Bioconjugation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022
    Article
  17. Article
  18. Article
  19. An Organometallic Strategy for Cysteine Borylation.Journal of the American Chemical Society · 2021
    Article
  20. Oligonucleotide Bioconjugation with Bifunctional Palladium Reagents.Angewandte Chemie (International ed. in English) · 2021
    Article
4 · The record

Corrections and comments

5 · Who and what money

Authors and funding

6 authors.

Heemal H DhanjeeMassachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.ORCID 0000-0002-3532-4430
Azin SaebiMassachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.
Ivan BuslovMassachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.
Alexander R LoftisMassachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.
Stephen L BuchwaldMassachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.ORCID 0000-0003-3875-4775
Bradley L PenteluteMassachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.ORCID 0000-0002-7242-801X

Funding

Treatments for Nipah Virus InfectionU54AI057159 · NIAID · HARVARD UNIVERSITY (MEDICAL SCHOOL) · PI FINBERG, ROBERT WILLIAM · 2003 to 2013
$113.7M
TOXICOLOGY CORE UNITP30ES002109 · NIEHS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI ENGELWARD, BEVIN P. · 1985 to 2020
$25.6M
Cysteine ArylationR01GM110535 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI PENTELUTE, BRADLEY LETHER · 2014 to 2018
$1.5M
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
NIAID NIH HHS U54 AI057159NIEHS NIH HHS P30 ES002109NIGMS NIH HHS F32 GM131592NIGMS NIH HHS R01 GM110535
6 · The paper itself

Abstract

Few chemical methods exist for the covalent conjugation of two proteins. We report the preparation of site-specific protein-protein conjugates that arise from the sequential cross-coupling of cysteine residues on two different proteins. The method involves the synthesis of stable palladium-protein oxidative addition complexes (Pd-protein OACs), a process that converts nucleophilic cysteine residues into an electrophilic S-aryl-Pd-X unit by taking advantage of an intramolecular oxidative addition strategy. This process is demonstrated on proteins up to 83 kDa in size and can be conveniently carried out in water and open to air. The resulting Pd-protein OACs can cross-couple with other thiol-containing proteins to arrive at homogeneous protein-protein bioconjugates.

Indexed as

CysteineModels, MolecularMolecular StructureOrganometallic CompoundsOxidation-ReductionPalladiumProtein BindingProteinsCysteineOrganometallic CompoundsPalladiumProteins

Identifiers

PMID32364380
PMCPMC7586714

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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.