N-Substituted Glycines with Functional Side-Chains for Peptoid Synthesis

摘要: N-Substituted glycines (NSG) constitute mimics of natural amino acids, and bring stability to peptide analogues. We developed a method synthesize NSG bearing reactive secondary heterofunctionality. It was shown that persilylation could be used for temporary protection groups present on the substrate, with aim selectively alkylating amine groups. ready coupling were obtained by C-terminal deprotection N-terminal resulting acid derivatives. This applied prepare N-alkylated as analogues serine, cysteine, tyrosine tryptophan. The last two derivatives in good yields N-homotyrosine (N-hTyr) has been introduced into sequence interest using automated solid-phase synthesis (SPPS).