An Expedient N-Terminal Attachment Methodology for the Solid Phase Peptide Synthesis

A general and successful N-terminal attachment methodology is described that allows the solid phase synthesis of oligopeptides from activated N-hydroxysuccinimide esters and amino acid lithium salts. The results of studies with different coupling systems for amide bond formation are presented. The oligomers were synthesized on solid support using a carbamate linker with final TFA/CH₂Cl₂ cleavage. This methodology was also applied for the preparation of peptide-substituted amides and esters in high purities and excellent yields.

N-hydroxysuccinimide esters - peptide-substituted amides - peptide esters - N-terminal attachment - solid-phase synthesis - amide formation