Synthesis of β-Thiol Phenylalanine for Applications in One-Pot Ligation–Desulfurization Chemistry

Lara R. Malins, Andrew M. Giltrap, Luke J. Dowman, and Richard J. Payne, Org. Lett., Article ASAP   Publication Date (Web): April 10, 2015   Copyright © 2015 American Chemical Society

The efficient synthesis of a β-thiol phenylalanine derivative is described starting from Garner’s aldehyde. The utility of this amino acid in peptide ligation–desulfurization chemistry is described, including the trifluoroethanethiol (TFET)-promoted one-pot assembly of the 62 residue peptide hormone augurin.