Peptide-derived self-assembled monolayers: adsorption of N-stearoyl L-cysteine methyl ester on gold

Journal of Molecular Recognition : JMR
S L Dawson, D A Tirrell

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.

References

Jan 1, 1986·Advances in Protein Chemistry·S Krimm, J Bandekar

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Citations

Apr 16, 1998·Journal of Pharmaceutical and Biomedical Analysis·K Kovács-Hadady, I Fábián
Oct 21, 2014·Chemical Communications : Chem Comm·Joe E BaioTobias Weidner
Aug 23, 2006·Leukemia & Lymphoma·Beverly P NelsonLoann C Peterson
Apr 6, 2005·Langmuir : the ACS Journal of Surfaces and Colloids·M M BeerbomR Schlaf

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