A convenient route to thiol terminated peptides for conjugation and surface functionalization strategies.

The derivatization of poly(p-(chloromethyl)styrene-co-divinylbenzene) (Merrifield resin) with N-(tert-butoxycarbonyl)-2-aminoethanethiol is presented as a convenient route for the generation of thiol terminated peptides using a solid phase methodology. Maximum resin substitution reached 92% (773 mumol/g) after 24 h. However, at 30 min, yields exceeded 400 mumol/g, above which the resin is suitable for solid phase peptide synthesis. Thiol terminated peptides are well-suited for subsequent chemical conjugation reactions or for the formation of organic monolayers on metal substrates.