Decarboxylative conjugate additions and applications thereof
AssigneeThe Trustees of Princeton University
InventorsDavid MacMillan, Daniel Novoa, Stefan McCarver
Life of this patent
Estimating the term…
Abstract
Synthetic methods are described herein operable to efficiently produce a wide variety of molecular species through conjugate additions via decarboxylative mechanisms. For example, methods of functionalization of peptide residues are described, including selective functionalization of peptide C-terminal residues. In one aspect, a method of peptide functionalization comprises providing a reaction mixture including a Michael acceptor and a peptide and coupling the Michael acceptor with the peptide via a mechanism including decarboxylation of a peptide reside.
Claims22
A method of conjugate addition comprising:
- providing a reaction mixture including a Michael acceptor and a substrate having a carboxyl group;
- and
- coupling the Michael acceptor and substrate via a mechanism including decarboxylative alkylation of the substrate.
A method of peptide functionalization comprising:
- providing a reaction mixture including a Michael acceptor and a peptide;
- and
- coupling the Michael acceptor with the peptide via a mechanism including decarboxylation, wherein the decarboxylation occurs subsequent to formation of a carboxyl radical at a peptide residue, the carboxyl radical formation being formed by a single electron transfer (SET) process initiated electrochemically.
A method of peptide functionalization comprising:
- providing a reaction mixture including a Michael acceptor, a peptide, and a photoredox catalyst;
- and
- coupling the Michael acceptor with the peptide via a mechanism including decarboxylation, wherein the decarboxylation occurs subsequent to formation of a carboxyl radical at a peptide residue, the carboxyl radical formation being formed by a single electron transfer (SET) process initiated by the photoredox catalyst.
Dependencies are inferred from the claim text.