Triblock Peptide and Peptide Thioester Synthesis With Reactivity-Differentiated Sulfonamides and Peptidyl Thioacids

摘要

With the construction of peptides by solid-phase peptide synthesis limited, for practical reasons, to chains of around fifty residues, the development of methods for the assembly of peptide blocks into longer sequences is of importance. Kent's concept of native chemical ligation was a major advance in this area, and has been considerably extended and optimized since its introduction in 1994. A significant number of these improvements have addressed the development of methods for peptidyl thioester synthesis and the limitations posed by the mechanistic requirement of using an N-terminal 2-mercaptoethylamine, typically cysteine. The most important modification, however, was the introduction, by Kent and co-workers, of the thiazolidine group as a means of protection for N-terminal cysteine moieties.