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

doi:10.1016/j.electacta.2008.01.002

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^*

^*Corresponding author for this work

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

12 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 language	English
Pages (from-to)	6209-6214
Number of pages	6
Journal	Electrochimica Acta
Volume	53
Issue number	21
DOIs	https://doi.org/10.1016/j.electacta.2008.01.002
Publication status	Published - 2008 Sept 1

Keywords

Catechin
Chiral recognition
Epicatechin
Homocysteine
Self-assembled monolayers

ASJC Scopus subject areas

Chemical Engineering(all)
Electrochemistry

Access to Document

10.1016/j.electacta.2008.01.002

Cite this

@article{d016c7ad7b654377b26ebf89c9d16e21,

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

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.",

keywords = "Catechin, Chiral recognition, Epicatechin, Homocysteine, Self-assembled monolayers",

author = "Takuya Nakanishi and Mariko Matsunaga and Makoto Nagasaka and Tsubasa Ueno and Tetsuya Osaka",

note = "Funding Information: This work was partly carried out in the Consolidated Research Institute for Advanced Science and Medical Care, Waseda University (ASMeW), which was financially supported by the Encouraging Development of Strategic Research Centers Program of the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan. MM acknowledges the grant-in-aid for JSPS Fellows, MEXT.",

year = "2008",

month = sep,

day = "1",

doi = "10.1016/j.electacta.2008.01.002",

language = "English",

volume = "53",

pages = "6209--6214",

journal = "Electrochimica Acta",

issn = "0013-4686",

publisher = "Elsevier Limited",

number = "21",

}

TY - JOUR

T1 - Stereospecificity in redox reactions of catechins at gold electrodes modified with self-assembled monolayers of homocysteine

AU - Nakanishi, Takuya

AU - Matsunaga, Mariko

AU - Nagasaka, Makoto

AU - Ueno, Tsubasa

AU - Osaka, Tetsuya

N1 - Funding Information: This work was partly carried out in the Consolidated Research Institute for Advanced Science and Medical Care, Waseda University (ASMeW), which was financially supported by the Encouraging Development of Strategic Research Centers Program of the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan. MM acknowledges the grant-in-aid for JSPS Fellows, MEXT.

PY - 2008/9/1

Y1 - 2008/9/1

N2 - 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.

AB - 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.

KW - Catechin

KW - Chiral recognition

KW - Epicatechin

KW - Homocysteine

KW - Self-assembled monolayers

UR - http://www.scopus.com/inward/record.url?scp=44949102302&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=44949102302&partnerID=8YFLogxK

U2 - 10.1016/j.electacta.2008.01.002

DO - 10.1016/j.electacta.2008.01.002

M3 - Article

AN - SCOPUS:44949102302

SN - 0013-4686

VL - 53

SP - 6209

EP - 6214

JO - Electrochimica Acta

JF - Electrochimica Acta

IS - 21

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this