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Synthesis and Structural Characterization of Glucopyranosylamide Films on Gold



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


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.
Journal of the American Chemical Society


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


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 July 17, 2024)


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Created January 16, 2007, Updated February 17, 2017