A traceless approach to amide and peptide construction from thioacids and dithiocarbamate-terminal amines Article

Chen, W, Shao, J, Hu, M et al. (2013). A traceless approach to amide and peptide construction from thioacids and dithiocarbamate-terminal amines . CHEMICAL SCIENCE, 4(3), 970-976. 10.1039/c2sc21317f

cited authors

  • Chen, W; Shao, J; Hu, M; Yu, W; Giulianotti, MA; Houghten, RA; Yu, Y

authors

abstract

  • A novel and traceless strategy has been devised that allows a coupling of thioacids and dithiocarbamate-terminal amines. This strategy had been assumed to be dependent on the attachment of a functional equivalent of a cysteine side chain in earlier native chemical ligation approaches. This approach enables the traceless removal of CS2 to directly generate the desired amide bond and is compatible with a range of unprotected side chains of amino acid. The ability to produce amide or peptides by a traceless removal of the auxiliary is a significant virtue of the method. Meanwhile, the application of this new peptide-bond-forming reaction to the synthesis of novel endomorphin (EM) derivatives with various binding potencies was realized. © 2013 The Royal Society of Chemistry.

publication date

  • March 1, 2013

published in

Digital Object Identifier (DOI)

start page

  • 970

end page

  • 976

volume

  • 4

issue

  • 3