Performance Comparison of Three Chemical Vapor Deposited Aminosilanes in Peptide Synthesis: Effects of Silane on Peptide Stability and Purity

Silicon oxide substrates underwent gas-phase functionalization with various aminosilanes, and the resulting surfaces were evaluated for their suitability as a solid support for solid phase peptide synthesis (SPPS). APTES (3-aminopropyltriethoxysilane), APDEMS (3-aminopropyldiethoxymethylsilane), and APDIPES (3-aminopropyldiisopropylethoxysilane) were individually applied to thermal oxide-terminated silicon substrates via gas-phase deposition. Coated surfaces were characterized by spectroscopic ellipsometry (SE), contact angle goniometry, X-ray photoelectron spectroscopy (XPS), atomic force microscopy (AFM), and spectrophotometry. Model oligopeptides with 16 residues were synthesized on the amino surfaces, and the chemical stabilities of the resulting surfaces were evaluated against a stringent side chain deprotection (SCD) step, which contained trifluoroacetic acid (TFA) and trifluoromethanesulfonic acid (TFMSA). Functionalized surface thickness loss during SCD was most acute for APDIPES and the observed ...