Enantioselectivity of redox reaction of DOPA at the gold electrode modified with a self-assembled monolayer of homocysteine

Takuya Nakanishi; Mariko Matsunaga; Makoto Nagasaka; Toru Asahi; Tetsuya Osaka

doi:10.1021/ja062380f

Enantioselectivity of redox reaction of DOPA at the gold electrode modified with a self-assembled monolayer of homocysteine

Takuya Nakanishi^*, Mariko Matsunaga, Makoto Nagasaka, Toru Asahi, Tetsuya Osaka

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

48 Citations (Scopus)

Abstract

The enantioselectivity of the self-assembled monolayer (SAM) of homocysteine formed on the (111)-oriented gold surface was investigated. We analyzed the redox behavior of 3,4-dihydroxyphenylalanine (DOPA), which is an electrochemically active chiral molecule, by means of cyclic voltammetry at a gold electrode modified with one enantiomeric form of homocysteine. It was demonstrated that the homocysteine SAM of one enantiomeric form blocked the redox reaction of only one enantiomer of DOPA, with cross inversion for the other enantiomer, in acidic solution.

Original language	English
Pages (from-to)	13322-13323
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	128
Issue number	41
DOIs	https://doi.org/10.1021/ja062380f
Publication status	Published - 2006 Oct 18

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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abstract = "The enantioselectivity of the self-assembled monolayer (SAM) of homocysteine formed on the (111)-oriented gold surface was investigated. We analyzed the redox behavior of 3,4-dihydroxyphenylalanine (DOPA), which is an electrochemically active chiral molecule, by means of cyclic voltammetry at a gold electrode modified with one enantiomeric form of homocysteine. It was demonstrated that the homocysteine SAM of one enantiomeric form blocked the redox reaction of only one enantiomer of DOPA, with cross inversion for the other enantiomer, in acidic solution.",

author = "Takuya Nakanishi and Mariko Matsunaga and Makoto Nagasaka and Toru Asahi and Tetsuya Osaka",

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T1 - Enantioselectivity of redox reaction of DOPA at the gold electrode modified with a self-assembled monolayer of homocysteine

AU - Nakanishi, Takuya

AU - Matsunaga, Mariko

AU - Nagasaka, Makoto

AU - Asahi, Toru

AU - Osaka, Tetsuya

PY - 2006/10/18

Y1 - 2006/10/18

N2 - The enantioselectivity of the self-assembled monolayer (SAM) of homocysteine formed on the (111)-oriented gold surface was investigated. We analyzed the redox behavior of 3,4-dihydroxyphenylalanine (DOPA), which is an electrochemically active chiral molecule, by means of cyclic voltammetry at a gold electrode modified with one enantiomeric form of homocysteine. It was demonstrated that the homocysteine SAM of one enantiomeric form blocked the redox reaction of only one enantiomer of DOPA, with cross inversion for the other enantiomer, in acidic solution.

AB - The enantioselectivity of the self-assembled monolayer (SAM) of homocysteine formed on the (111)-oriented gold surface was investigated. We analyzed the redox behavior of 3,4-dihydroxyphenylalanine (DOPA), which is an electrochemically active chiral molecule, by means of cyclic voltammetry at a gold electrode modified with one enantiomeric form of homocysteine. It was demonstrated that the homocysteine SAM of one enantiomeric form blocked the redox reaction of only one enantiomer of DOPA, with cross inversion for the other enantiomer, in acidic solution.

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Enantioselectivity of redox reaction of DOPA at the gold electrode modified with a self-assembled monolayer of homocysteine

Abstract

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