Peptides, bromination, solid-phase

The first successful solid-phase synthesis of a peptide (H-Leu-Ala-Gly-Val-OH) was reported by Merrifield in 1963 [12]. The strategy used is outlined in Figure 16.1. The support was chloromethylated, partially nitrated (or brominated), 2% cross-linked polystyrene. Nitration was necessary to suppress acidolytic cleavage of the benzyl ester attachment during Z-group removal. Acylations of deprotected, support-bound amino acids were performed with DCC, and at the end of the synthesis the peptide was cleaved from the support by saponification with sodium hydroxide. 

---