Solid phase organic synthesis of pegylated disulfides for the generation of biocompatible self-assembled monolayers

COLL 198

Lu Shin Wong, l.s.wong@manchester.ac.uk1, Stefan J. Janusz, s.janusz@shef.ac.uk2, Graham J Leggett, Graham.Leggett@shef.ac.uk2, and Jason Micklefield1. (1) Manchester Interdisciplinary Biocentre, University of Manchester, 131 Princess Street, Manchester, M1 7DN, United Kingdom, (2) Department of Chemistry, University of Sheffield, Dainton Building, Brook Hill, Sheffield, S3 7HF, United Kingdom
Self-assembled monolayers (SAMs) of alkylthiolates on metals are used in studies of biomolecular interactions and in the development of protein arrays. However, their full exploitation requires SAMs which resist non-specific adsorption of biomolecules while providing the means for the attachment of a range ligands at specific locations on the surfaces. There is therefore a need for a generally applicable method for the facile generation such alkanethiols or their equivalents. Here, the application of a solid phase synthetic strategy for the modular synthesis of pegylated alkanedisulfides 1 and 2 is reported. The synthesis of the required building blocks, their assembly on a 4-methoxytrityl polstyrene support, and subsequent cleavage and purification are described. SPR & XPS experiments further demonstrate that SAMs of 1 are stable and resist non-specific protein adsorption.

 

Fundamental Research in Colloid and Surface Chemistry
6:00 PM-8:00 PM, Monday, August 20, 2007 BCEC -- East Registration, Poster

Division of Colloid & Surface Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007