Fig. 4: Biocompatible decarboxylative coupling of peptides in solid-phase synthesis.
From: Biocompatible decarboxylative coupling enabled by N-hydroxynaphthalimide esters
Three peptides 73, 75, 77 containing carboxyl groups were synthesized on solid-phase resin. The carboxyl groups were in situ activated and converted to NHNI esters, followed by reaction with silyl enol ether 4 in 50% DMSO/Tris buffer. After the reaction, the peptides were cleaved from the resin to yield 74, 76 and 78 bearing ketone functional groups. This demonstrates the applicability of solid-phase synthesis for decarboxylative alkylation of peptides, providing a general method for peptide modification. NHNI ester N-hydroxynaphthalimide ester, TMS trimethylsilyl, DMSO dimethyl sulfoxide, SPPS solid-phase peptide synthesis.
