Chemical Description: 11-Amino-1-undecanethiol, hydrochloride
Appearance: White or slightly reddish white crystalline powder
Purity: ≥90.0% (HPLC, derivatization)
MW: 239.85, C11
Storage Condition: -20
ºC, protect from light and metal
Shipping Condition: ambient temperature
Aminoalkanethiols are utilized for the modification of a gold surface to introduce amino groups on the surface. Dojindo’s newly developed 16-Amino-1-hexadecanethiol has a 16-carbon chain, which is the longest alkanethiol available in the market. It is expected that 16-Amino-1-hexadecanethiolwill form the most stable SAM on a gold surface among the aminoalkanethiol compounds because of the greater Van-der-Waals force between alkane groups. Five different aminoalkanethiols including Amino-EG6-undecanethiol, hydrochloride are available for gold surface modification. Amino-EG6-undecanethiol is used for hydrophilic surface preparation. The amino group is usually modified using aminereactivematerials, such as proteins or biomaterials, to functionalize the gold surface. Several researchers have reported SAMs of short alkylchain aminoalkanethiols, and there are an increasing number of reports of long alkyl chain compounds. Takahara and others formed a monolayer of 11-Amino-1-undecanethiol on a gold electrode and studied the effect of the terminal groups on the redox responses of ferrocene derivatives using the voltammetric method. They also reported the relationship between the alkyl chain length of aminoalkanethiols and the redox behavior of 2,3-dichloro-1,4-naphtoquinone attached to the terminal amino group. Tanahashi and coworkers modified a gold surface with SAMs of several kinds of functionalized alkanethiols. They reported the effect of their terminal functional groups on apatite formation in a simulated body fluid using X-ray photoelectron spectroscopic (XPS) measurement and quartz crystal microbalance (QCM) method.
How to prepare the SPR-Chip: Link to Application Note
1. J. M. Brockman, A. G. Frutos and R. M. Corn, A Multistep Chemical Modification Procedure To Create DNA Arrays on Gold Surface for the Study of Protein-DNA Interactions with Surface Plasmon Resonance Imaging, J. Am. Chem. Soc., 1999, 121, 8044.
2. Y. Yoshimi, T. Matsuda, Y. Itoh, F. Ogata and T. Katsube, Surface Modifications of Functional Electrodes of a Light Addressable Potentiometric Sensor (LAPS): Non-Dependency of pH Sensitivity on the Surface Functional Group, Mater. Sci. Eng. C, 1997, 5, 131.
3. M. Tanahashi and T. Matsuda, Surface Functional Group Dependence on Apatite Formation on Self-assembled Monolayers in a Simulated Body Fluid, J. Biomed. Mater. Res., 1997, 34, 305.
4. J. Tien, A. Terfort and G. M. Whitesides, Microfaburication through Electrostatic Self-Assembly, Langmuir, 1997, 13, 5349.
5. F. Mukae, H. Takemura and K. Takehara, Electrochemical Behavior of the Naphtoquinone Anchored onto a Gold Electrode through the Self-Assembled monolayers of Aminoalkanethiol, Bull. Chem. Soc. Jpn., 1996, 69, 2461.
6. S. Rubin, G. Bar, R. W. Cutts, J. T. Chow, J. P. Ferraris, and T. A. Zawodzinski, Electrical Communication Between Glucose Oxidase and Different Ferrocenylalkanethiol Chain Lengths, Mater. Res. Soc. Symp. Proc., 1996, 413, 377.
7. K. Takehara and H. Takemura, Electrochemical Behaviors of Ferrocene Derivatives at an Electrode Modified with Terminally Substituted Alkanethiol Monolayer Assemblies, Bull. Chem. Soc. Jpn., 1995, 68, 1289.
8. K. Takehara, H. Takemura and Y. Ide, Electrochemical Studies of the Terminally Substituted Alkanethiol Monolayers Formed on a Gold Electrode; Effect of the Terminal Group on the Redox Responses of Fe(CN)63-,Ru(NH3)63+ and Ferrocenedimethanol, Electrochim. Acta, 1994, 39, 817.
9. H. J. Lee, A. W. Wark, Y. Li and R. M. Corn, Fabricating RNA Microarrays with RNA-DNA Surface Ligation Chemistry, Anal. Chem., 2005, 77, 7832.