Stepwise synthesis of Gly-Gly-His on gold surfaces modified with mixed self-assembled monolayers.
Peptide-modified electrode surfaces have been shown to have excellent recognition properties for metal ions. An efficient method of screening a potential peptide for its selectivity for a given metal would involve the synthesis of the peptide directly on the electrode surface. This paper outlines a procedure in which the tripeptide Gly-Gly-His was synthesized one amino acid at a time on a gold surface modified with a self-assembled monolayer of the mixed alkanethiolates 3-mercaptopropionic acid (MPA) and 3-mercaptopropane (MP). Electrochemistry and high-resolution mass spectrometry were used to elucidate the structure of the adsorbed species and follow the synthesis. The amino acids can be attached only to MPA, but the presence of a diluting unreactive molecule of MP reduces steric crowding about the reaction center. The maximum coverage of synthesized tripeptide occurs at a ratio of MPA/MP of 1:1.
Yang
Wenrong R
WR
School of Chemistry, The University of New South Wales, Sydney 2052, Australia.
Hibbert
D Brynn
DB
Zhang
Rui
R
Willett
Gary D
GD
Gooding
J Justin
JJ
D015097:3-Mercaptopropionic Acid / Q000737:chemistry; D004563:Electrochemistry; D004566:Electrodes; D005998:Glycine / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D006639:Histidine / Q000737:chemistry*; D013058:Mass Spectrometry; D009842:Oligopeptides / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared
D009842:Oligopeptides; D006639:Histidine; D006046:Gold; D015097:3-Mercaptopropionic Acid; D005998:Glycine