‘Volatilizable’ Supports for High-Throughput Organic Synthesis

Significance

‘Volatilizable’ solid supports for solid-phase peptide synthesis were developed. Silica-based solid supports were decomposed by HF to afford volatile SiF₄ and water in the final cleavage step of peptide syntheses (tri- to pentapeptides), which were easily removed by evaporation or lyophilization. In the final cleavage step, C- and N-terminal-protected peptides were obtained selectively (91-98% yield) by using 10% aqueous HF (for 1 h at r.t., 5 examples) and N-acylation followed by anhydrous HF (for 1.5 h at 0 °C, 3 examples), respectively. The automated peptide syntheses were also performed to give tetrapeptides in ca. 90% yields (2 examples).