Formation of a self-assembled phenylboronic acid monolayer and its application toward developing a surface plasmon resonance-based monosaccharide sensor

For the surface-optoelectronic study of sugar sensing, we synthesized and characterized dithiobis(4-butyrylamino-m-phenylboronic acid) (DTBA-PBA) as a recognition molecule. DTBA-PBA has a boronic acid group that has been known to form covalently bonded complexes with the 1,2- or 1,3-diol of sugars. A self-assembled monolayer (SAM) of DTBA-PBA was formed on a gold surface and characterized by atomic-force microscopy, Fourier transform infrared reflection absorption spectroscopy, and surface electrochemical measurements. An interaction study between monosaccharides and DTBA-PBA SAM was performed using surface plasmon resonance spectroscopy. The increase in molecular interactions between DTBA-PBA SAM and monosaccharides resulted in an optically induced electron excitation change on the Au surface through a refractive index change of the interfacial recognition layer. This correlation between electron excitation and molecular interaction was measurable at very low monosaccharide concentrations (1.0 x 10(-12) M). DTBA-PBA SAM shows a selective fructose sensing among four kinds of monosaccharides, even in a low concentration range. (C) 2002 Elsevier Science (USA). All rights reserved.