Application of (2E,4E)-5-Bromo-2,4-Pentadienal in Palladium Catalyzed Cross-Coupling: Easy Access to (2E,4E)-2,4-Dienals

Synlett ◽  
1998 ◽  
Vol 1998 (4) ◽  
pp. 411-412 ◽  
Author(s):  
Nicolas Vicart ◽  
Dominique Castet-Caillabet ◽  
Yvan Ramondenc ◽  
Gérard Plé ◽  
Lucette Duhamel
Keyword(s):  
Cross Coupling ◽  
Easy Access ◽  
Palladium Catalyzed

Palladium-catalyzed 3-Thiomethyltriazine-boronic Acid Cross Coupling: Easy Access to 3-Substituted-1,2,4-triazines

Synlett ◽  
2002 ◽  
Vol 2002 (03) ◽  
pp. 0447-0450 ◽  
Author(s):  
France-Aimée Alphonse ◽  
Franck Suzenet ◽  
Anne Keromnes ◽  
Bruno Lebret ◽  
Gérald Guillaumet
Keyword(s):  
Boronic Acid ◽  
Cross Coupling ◽  
Easy Access ◽  
Palladium Catalyzed

ChemInform Abstract: Application of (2E,4E)-5-Bromo-2,4-pentadienal in Palladium-Catalyzed Cross-Coupling: Easy Access to (2E,4E)-2,4-Dienals.

ChemInform ◽  
2010 ◽  
Vol 29 (28) ◽  
pp. no-no
Author(s):  
N. VICART ◽  
D. CASTET-CAILLABET ◽  
Y. RAMONDENC ◽  
G. PLE ◽  
L. DUHAMEL
Keyword(s):  
Cross Coupling ◽  
Easy Access ◽  
Palladium Catalyzed

ChemInform Abstract: Palladium-Catalyzed 3-Thiomethyltriazine-boronic Acid Cross Coupling: Easy Access to 3-Substituted-1,2,4-triazines.

ChemInform ◽  
2010 ◽  
Vol 33 (30) ◽  
pp. no-no
Author(s):  
France-Aimee Alphonse ◽  
Franck Suzenet ◽  
Anne Keromnes ◽  
Bruno Lebret ◽  
Gerald Guillaumet
Keyword(s):  
Boronic Acid ◽  
Cross Coupling ◽  
Easy Access ◽  
Palladium Catalyzed

Suzuki–Miyaura cross-coupling for chemoproteomic applications

2020 ◽  
Author(s):  
Jian Cao ◽  
Ernest Armenta ◽  
Lisa Boatner ◽  
Heta Desai ◽  
Neil Chan ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Cross Coupling ◽  
Protein Profiling ◽  
Protein Labeling ◽  
Caspase 8 ◽  
Complex Cell ◽  
Bioorthogonal Chemistry ◽  
Reaction Conditions ◽  
Target Deconvolution ◽  
Palladium Catalyzed

Bioorthogonal chemistry is a mainstay of chemoproteomic sample preparation workflows. While numerous transformations are now available, chemoproteomic studies still rely overwhelmingly on copper-catalyzed azide –alkyne cycloaddition (CuAAC) or 'click' chemistry. Here we demonstrate that gel-based activity-based protein profiling (ABPP) and mass-spectrometry-based chemoproteomic profiling can be conducted using Suzuki–Miyaura cross-coupling. We identify reaction conditions that proceed in complex cell lysates and find that Suzuki –Miyaura cross-coupling and CuAAC yield comparable chemoproteomic coverage. Importantly, Suzuki–Miyaura is also compatible with chemoproteomic target deconvolution, as demonstrated using structurally matched probes tailored to react with the cysteine protease caspase-8. Uniquely enabled by the observed orthogonality of palladium-catalyzed cross-coupling and CuAAC, we combine both reactions to achieve dual protein labeling.

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