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.
Winger
T M
TM
School of Chemical Engineering, Georgia Institute of Technology, Atlanta 30332, USA.
Ludovice
P J
PJ
Chaikof
E L
EL
D000595:Amino Acid Sequence; D002219:Carbamates / Q000737:chemistry; D007202:Indicators and Reagents; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis*; D011137:Polystyrenes / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D002219:Carbamates; D007202:Indicators and Reagents; C095039:Merrifield resin; D010455:Peptides; D011137:Polystyrenes; D013438:Sulfhydryl Compounds; C095040:N-(tert-butoxycarbonyl)-2-aminoethanethiol