Zirconocene dichloride (Cp(2)ZrCl(2)) has been shown to be an effective catalyst for the transamidation of primary amides with amines in cyclohexane at 80 °C in 5-24 hours. For favourable substrates, the reaction can be performed at temperatures as low as 30 °C.
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http://dx.doi.org/10.1039/c2cc37427g | DOI Listing |
Org Biomol Chem
August 2024
College of Agronomy, Hunan Agricultural University, Changsha 410128, People's Republic of China.
A BF·OEt-mediated transamidation between unactivated amides and amines is reported, enabling access to diverse secondary and tertiary amides under transition-metal-free and solvent-free conditions. The operationally simple procedure provides a novel manifold for converting amide-amide bonds with excellent chemoselectivity. In particular, a series of amides including challenging thioamides enable direct transamidation to products with modest to excellent yields.
View Article and Find Full Text PDFPLoS One
May 2024
Immunology Therapeutic Area, UCB Pharma, Slough, United Kingdom.
Fibrotic remodeling is the primary driver of functional loss in chronic kidney disease, with no specific anti-fibrotic agent available for clinical use. Transglutaminase 2 (TG2), a wound response enzyme that irreversibly crosslinks extracellular matrix proteins causing dysregulation of extracellular matrix turnover, is a well-characterized anti-fibrotic target in the kidney. We describe the humanization and characterization of two anti-TG2 monoclonal antibodies (zampilimab [hDC1/UCB7858] and BB7) that inhibit crosslinking by TG2 in human in vitro and rabbit/cynomolgus monkey in vivo models of chronic kidney disease.
View Article and Find Full Text PDFBioconjug Chem
April 2024
Department of Chemistry and Chemical Biology, Barnett Institute of Chemical and Biological Analysis, Northeastern University, Boston, Massachusetts 02115, United States.
A versatile chemo-enzymatic tool to site-specifically modify native (nonengineered) antibodies is using transglutaminase (TGase, E.C. 2.
View Article and Find Full Text PDFChem Commun (Camb)
February 2024
Centre for Membrane Separations, Adsorption, Catalysis and Spectroscopy for Sustainable Solutions (cMACS), KU Leuven, 3001 Leuven, Belgium.
The transamidation of polyamides with short primary amides is reported as an effective recycling technique. This novel depolymerization method is robust and only utilizes cheap and renewable reagents. The process requires a NbO catalyst, assisted by NH, and operates at relatively mild reaction conditions ( 200 °C and 3 bar NH).
View Article and Find Full Text PDFJ Org Chem
January 2024
National Engineering Research Center for Carbohydrate Synthesis, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China.
The C-N bond transamidation of primary amides with ,-dimethyl enaminones has been efficiently realized by heating in the presence of trifluoromethanesulfonic acid (TfOH). The method enables the practical synthesis of valuable enamides without the use of any metal reagent. In addition, this transamidation protocol can also be expanded to the reactions of sulfonamides, and the late-stage functionalization on sulfonamide drugs such as Celecoxib and Valdecoxib has been verified.
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