10604-70-3Relevant articles and documents
Radical-Mediated Acyl Thiol-Ene Reaction for Rapid Synthesis of Biomolecular Thioester Derivatives
Lynch, Dylan M.,McLean, Joshua T.,McSweeney, Lauren,Milbeo, Pierre,Scanlan, Eoin M.
, p. 4148 - 4160 (2021)
The thiol-ene ‘click’ reaction has emerged as a versatile process for carbon–sulfur bond formation with widespread applications in chemical biology, medicinal chemistry and materials science. Thioesters are key intermediates in a wide range of synthetic and biological processes and efficient methods for their synthesis are of considerable interest. Herein, we report the first examples of acyl-thiol-ene (ATE) for the synthesis of biomolecular thioesters, including peptide, lipid and carbohydrate derivatives. A key finding is the profound effect of the amino acid side chain on the outcome of the ATE reaction. Furthermore, radical generated thioesters underwent efficient S-to-N acyl transfer and desulfurisation to furnish ‘sulfur-free’ ligation products in an overall amidation process with diverse applications for chemical ligation and bioconjugation.
Facile Catalytic Conversion of Carboxylic Acids into Thiocarboxylic S-Acids by the Ph3SbO/P4S10 System
Nomura, Ryoki,Miyazaki, Shin-Ichiro,Nakano, Takahiro,Matsuda, Haruo
, p. 2081 - 2082 (2007/10/02)
Thiocarboxylic S-acids 2 are readily prepared by direct sulfuration of the corresponding carboxylic acids 1 catalyzed by Ph3SbO/P4S10 under mild conditions.
