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Synthesis and Structural Characterization of Glucopyranosylamide Films on Gold

Published

Author(s)

Mridula Kadalbajoo, J J. Park, A Opdahl, Hiromi Suda, Kitchens A. C, Jayne C. Garno, J Batteas, Michael J. Tarlov, Phillip DeShong

Abstract

Stereoselective synthesis of a- and b-linked glucopyranosylamide derivatives via the in situ generation of glucosyl isoxazolines has been performed utilizing a modified Staudinger methodology. Glucopyranosylamides were derivatized with thiol functionalities and adsorbed on gold surfaces from ethanol solutions. The resulting film structures were characterized by atomic force microscopy (AFM), reflection Fourier-transform infrared (FTIR) spectroscopy, and X-ray photoelectron spectroscopy (XPS). The experimental data indicate that a- or b-linked glucopyranosyl derivatives with free hydroxyl groups attach to gold via the thiol linker. Both derivatives form monolayer films with high packing densities - comparable to those typically observed for alkanethiol monolayers on gold.
Citation
Journal of the American Chemical Society
Volume
23
Issue
2

Keywords

AFM, FTIR, oligosccharide, self-assembled monolayers, stereospecific, synthesis, XPS

Citation

Kadalbajoo, M. , Park, J. , Opdahl, A. , Suda, H. , C, K. , Garno, J. , Batteas, J. , Tarlov, M. and DeShong, P. (2007), Synthesis and Structural Characterization of Glucopyranosylamide Films on Gold, Journal of the American Chemical Society (Accessed April 14, 2024)
Created January 16, 2007, Updated February 17, 2017