Stereospecificity in redox reactions of catechins at gold electrodes modified with self-assembled monolayers of homocysteine

Takuya Nakanishi, Mariko Matsunaga, Makoto Nagasaka, Tsubasa Ueno, Tetsuya Osaka

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

The stereospecificity of a self-assembled monolayer (SAM) of homocysteine formed on the (1 1 1)-oriented gold surface toward the molecules with two chiral centers was investigated. Redox behaviors of catechins, which are electrochemically active molecules with two chiral centers, were analyzed with cyclic voltammetry by using a gold electrode modified with one enantiomeric form of homocysteine. The homocysteine SAM of one enantiomeric form was demonstrated to block the redox reaction of one enantiomer of catechin or epicatechin greater than that of the other, with cross inversion for the other enantiomer, in acidic solution. In addition, the homocysteine SAM on the gold electrode was suggested to recognize the chirality of one of the two chiral centers in catechin and epicatechin.

Original languageEnglish
Pages (from-to)6209-6214
Number of pages6
JournalElectrochimica Acta
Volume53
Issue number21
DOIs
Publication statusPublished - 2008 Sep 1

Fingerprint

Catechin
Redox reactions
Self assembled monolayers
Homocysteine
Gold
Enantiomers
Electrodes
Molecules
Chirality
Cyclic voltammetry

Keywords

  • Catechin
  • Chiral recognition
  • Epicatechin
  • Homocysteine
  • Self-assembled monolayers

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Analytical Chemistry
  • Electrochemistry

Cite this

Stereospecificity in redox reactions of catechins at gold electrodes modified with self-assembled monolayers of homocysteine. / Nakanishi, Takuya; Matsunaga, Mariko; Nagasaka, Makoto; Ueno, Tsubasa; Osaka, Tetsuya.

In: Electrochimica Acta, Vol. 53, No. 21, 01.09.2008, p. 6209-6214.

Research output: Contribution to journalArticle

Nakanishi, Takuya ; Matsunaga, Mariko ; Nagasaka, Makoto ; Ueno, Tsubasa ; Osaka, Tetsuya. / Stereospecificity in redox reactions of catechins at gold electrodes modified with self-assembled monolayers of homocysteine. In: Electrochimica Acta. 2008 ; Vol. 53, No. 21. pp. 6209-6214.
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