title: Peptide-derived self-assembled monolayers: adsorption of N-stearoyl L-cysteine methyl ester on gold.
abstract: The work reported herein concerns the assembly of N-stearoyl L-cysteine methyl ester [CH3(CH2)16COCysOMe, 1] on the surface of gold. This compound serves as a simple model of a related polypeptide, which has been designed to adopt a beta-sheet architecture on metallic and oxide surfaces. We describe the preparation of monolayers of 1, and characterization of these layers via ellipsometry, vibrational spectroscopy and X-ray photoelectron spectroscopy. The results are most consistent with a disordered array of the alkyl chains, in which close packing is frustrated by a mismatch in the cross-sectional areas of the cysteinyl ester head group and the stearoyl chains of the thiol. Despite the disorder, the alkyl chains form a hydrophobic surface layer, with an advancing contact angle for water comparable to that observed for octadecanethiol on gold.
authors.affiliation: Polymer Science and Engineering Department, University of Massachusetts at Amherst 01003, USA.
authors.forename: S L
authors.initials: SL
authors.lastname: Dawson
authors.forename: D A
authors.initials: DA
authors.lastname: Tirrell
mesh_terms: D000327:Adsorption; D003545:Cysteine / Q000031:analogs & derivatives* / Q000737:chemistry; D006046:Gold / Q000737:chemistry*; D006860:Hydrogen Bonding; D010455:Peptides / Q000737:chemistry*; D013052:Spectrometry, X-Ray Emission / Q000379:methods; D017550:Spectroscopy, Fourier Transform Infrared / Q000379:methods; D013329:Structure-Activity Relationship; D013499:Surface Properties
chemical_list: C107382:N-stearoyl cysteine methyl ester; D010455:Peptides; D006046:Gold; D003545:Cysteine; C017507:mecysteine