Theonellamide C (1  ) is a bicyclic peptide that is distinguished by its crosslinking t-histidinoalanine (t-HAL) residue. Histidinoalanine is a bis-amino acid that was first isolated in 1982 from the hydrolysate of human dentine collagen and has subsequently been found in human tissues, milk products, and theonellamide related peptides. The aim of this investigation was to synthesize a fully orthogonally protected t-HAL (2  ) residue that can be incorporated into Theonellamide C and features the coupling of Boc-His-OMe (3  ) and sulfamidate (4  ) derived from Fmoc-D-Ser-OtBu. The subsequent selective deprotection of each protecting group will be elaborated.

Synthesis of [tau]-histidinoalanine via a cyclic sulfamidate: A quadrupal orthogonal protecting group study

244th National Meeting (2012)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.