Effect of pH on the Enantiospecificity of Homocysteine Monolayer on Au(111) for the Redox Reaction of 3,4‐Dihydroxyphenylalanine | Zendy

Matsunaga Mariko | Zendy; Nagasaka Makoto | Zendy; Nakanishi Takuya | Zendy; Sawaguchi Takahiro | Zendy; Osaka Tetsuya | Zendy

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Effect of pH on the Enantiospecificity of Homocysteine Monolayer on Au(111) for the Redox Reaction of 3,4‐Dihydroxyphenylalanine

Author(s) -

Matsunaga Mariko,

Nagasaka Makoto,

Nakanishi Takuya,

Sawaguchi Takahiro,

Osaka Tetsuya

Publication year - 2008

Publication title -

electroanalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.574

H-Index - 128

eISSN - 1521-4109

pISSN - 1040-0397

DOI - 10.1002/elan.200704110

Subject(s) - chemistry , dimer , monolayer , redox , dihydroxyphenylalanine , molecule , electrochemistry , scanning tunneling microscope , hydrogen bond , stereochemistry , homocysteine , electrode , inorganic chemistry , organic chemistry , biochemistry , nanotechnology , neuroscience , dopamine , biology , materials science

The effect of pH on the enantiospecificity of Au (111) electrode modified with L ‐homocysteine was evaluated for the electrochemical redox reaction of 3,4‐dihydroxyphenylalanine (DOPA). Cyclic voltammetric peaks clearly exhibited enantiospecificity at pH 0.6 and 2, whereas no enantiospecificity was observed at pH 3, 4, and 5.5. Scanning tunneling microscopy confirmed the highly ordered (2√3×3√3)R30° structure of L ‐homocysteine at pH 0.6, at which L ‐homocysteine molecules form a dimer through the hydrogen‐bond between carboxy groups (COOH), while a disordered structure was observed at pH 5.5. These results suggest that the dimer formed in the acidic solutions at pH below 3 plays an important role in providing the enantiospecificity to the Au(111) surface.

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