Effect of surface coverage of gold(111) electrode with cysteine on the chiral discrimination of DOPA

Mariko Matsunaga, Takuya Nakanishi, Toru Asahi, Tetsuya Osaka

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The enantioselectivity imparted to a gold electrode by modifying its surface with a self-assembled monolayer (SAM) of cysteine (Cys) was investigated for the electrochemical redox reaction of 3,4-dihydroxyphenylalanine (DOPA). A cyclic voltammetric study of the redox reaction revealed that the enantioselectivity was determined by the surface coverage of the gold electrode with Cys molecules. The electrode modified with ∼1.8 × 1014 Cys molecules cm-2 exhibited enantioselectivity in the voltammogram for the oxidation and reduction of DOPA, while the voltammograms obtained by the electrodes with either more or less surface coverages did not exhibit significant enantioselectivity. It is suggested that the accessibility of DOPA to that area of the gold surface which is not blocked by Cys molecules at an optimum surface coverage, is required for the enantioselective redox reaction of DOPA to proceed.

Original languageEnglish
Pages (from-to)295-299
Number of pages5
JournalChirality
Volume19
Issue number4
DOIs
Publication statusPublished - 2007

Fingerprint

Dihydroxyphenylalanine
Gold
Enantioselectivity
Oxidation-Reduction
Cysteine
Electrodes
Redox reactions
Molecules
Self assembled monolayers
Oxidation

Keywords

  • Amino acids
  • Chiral discrimination
  • Chiral sensing
  • Cyclic voltammetry
  • Electrochemical method
  • Self-assembled monolayers

ASJC Scopus subject areas

  • Analytical Chemistry
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Effect of surface coverage of gold(111) electrode with cysteine on the chiral discrimination of DOPA. / Matsunaga, Mariko; Nakanishi, Takuya; Asahi, Toru; Osaka, Tetsuya.

In: Chirality, Vol. 19, No. 4, 2007, p. 295-299.

Research output: Contribution to journalArticle

@article{cf39894ae19e458186af231dd17c4042,
title = "Effect of surface coverage of gold(111) electrode with cysteine on the chiral discrimination of DOPA",
abstract = "The enantioselectivity imparted to a gold electrode by modifying its surface with a self-assembled monolayer (SAM) of cysteine (Cys) was investigated for the electrochemical redox reaction of 3,4-dihydroxyphenylalanine (DOPA). A cyclic voltammetric study of the redox reaction revealed that the enantioselectivity was determined by the surface coverage of the gold electrode with Cys molecules. The electrode modified with ∼1.8 × 1014 Cys molecules cm-2 exhibited enantioselectivity in the voltammogram for the oxidation and reduction of DOPA, while the voltammograms obtained by the electrodes with either more or less surface coverages did not exhibit significant enantioselectivity. It is suggested that the accessibility of DOPA to that area of the gold surface which is not blocked by Cys molecules at an optimum surface coverage, is required for the enantioselective redox reaction of DOPA to proceed.",
keywords = "Amino acids, Chiral discrimination, Chiral sensing, Cyclic voltammetry, Electrochemical method, Self-assembled monolayers",
author = "Mariko Matsunaga and Takuya Nakanishi and Toru Asahi and Tetsuya Osaka",
year = "2007",
doi = "10.1002/chir.20376",
language = "English",
volume = "19",
pages = "295--299",
journal = "Chirality",
issn = "0899-0042",
publisher = "Wiley-Liss Inc.",
number = "4",

}

TY - JOUR

T1 - Effect of surface coverage of gold(111) electrode with cysteine on the chiral discrimination of DOPA

AU - Matsunaga, Mariko

AU - Nakanishi, Takuya

AU - Asahi, Toru

AU - Osaka, Tetsuya

PY - 2007

Y1 - 2007

N2 - The enantioselectivity imparted to a gold electrode by modifying its surface with a self-assembled monolayer (SAM) of cysteine (Cys) was investigated for the electrochemical redox reaction of 3,4-dihydroxyphenylalanine (DOPA). A cyclic voltammetric study of the redox reaction revealed that the enantioselectivity was determined by the surface coverage of the gold electrode with Cys molecules. The electrode modified with ∼1.8 × 1014 Cys molecules cm-2 exhibited enantioselectivity in the voltammogram for the oxidation and reduction of DOPA, while the voltammograms obtained by the electrodes with either more or less surface coverages did not exhibit significant enantioselectivity. It is suggested that the accessibility of DOPA to that area of the gold surface which is not blocked by Cys molecules at an optimum surface coverage, is required for the enantioselective redox reaction of DOPA to proceed.

AB - The enantioselectivity imparted to a gold electrode by modifying its surface with a self-assembled monolayer (SAM) of cysteine (Cys) was investigated for the electrochemical redox reaction of 3,4-dihydroxyphenylalanine (DOPA). A cyclic voltammetric study of the redox reaction revealed that the enantioselectivity was determined by the surface coverage of the gold electrode with Cys molecules. The electrode modified with ∼1.8 × 1014 Cys molecules cm-2 exhibited enantioselectivity in the voltammogram for the oxidation and reduction of DOPA, while the voltammograms obtained by the electrodes with either more or less surface coverages did not exhibit significant enantioselectivity. It is suggested that the accessibility of DOPA to that area of the gold surface which is not blocked by Cys molecules at an optimum surface coverage, is required for the enantioselective redox reaction of DOPA to proceed.

KW - Amino acids

KW - Chiral discrimination

KW - Chiral sensing

KW - Cyclic voltammetry

KW - Electrochemical method

KW - Self-assembled monolayers

UR - http://www.scopus.com/inward/record.url?scp=34247539386&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34247539386&partnerID=8YFLogxK

U2 - 10.1002/chir.20376

DO - 10.1002/chir.20376

M3 - Article

C2 - 17345562

AN - SCOPUS:34247539386

VL - 19

SP - 295

EP - 299

JO - Chirality

JF - Chirality

SN - 0899-0042

IS - 4

ER -