Synthesis of a Novel Cysteine-Incorporated Anthraquinone Derivative and Its Structural Properties

Akihiro Nomoto; Toshihide Taniguchi; Yuta Minatobe; Syouhei Katao; Kiyomi Kakiuchi; Shigenobu Yano; Akiya Ogawa

doi:10.3390/molecules200610192

Synthesis of a Novel Cysteine-Incorporated Anthraquinone Derivative and Its Structural Properties

Molecules. 2015 Jun 3;20(6):10192-204. doi: 10.3390/molecules200610192.

Authors

Akihiro Nomoto¹, Toshihide Taniguchi^{2

3}, Yuta Minatobe⁴, Syouhei Katao⁵, Kiyomi Kakiuchi⁶, Shigenobu Yano⁷, Akiya Ogawa⁸

Affiliations

¹ Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Nakaku, Sakai, Osaka 599-8531, Japan. nomoto@chem.osakafu-u.ac.jp.
² Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Nakaku, Sakai, Osaka 599-8531, Japan. tttoshihide1@yahoo.co.jp.
³ Seika Corporation, 1-1-82 Kozaika, Wakayama 641-0007, Japan. tttoshihide1@yahoo.co.jp.
⁴ Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Nakaku, Sakai, Osaka 599-8531, Japan. yuta_minatobe@shokubai.co.jp.
⁵ Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5, Takayama, Ikoma, Nara 630-0192, Japan. katao@ms.naist.jp.
⁶ Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5, Takayama, Ikoma, Nara 630-0192, Japan. kakiuchi@ms.naist.jp.
⁷ Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5, Takayama, Ikoma, Nara 630-0192, Japan. yano-shigenobu@ms.naist.jp.
⁸ Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Nakaku, Sakai, Osaka 599-8531, Japan. ogawa@chem.osakafu-u.ac.jp.

Abstract

A novel cysteine-incorporated anthraquinone derivative was synthesized, and its molecular structure was determined by X-ray crystal analysis. Each mercapto group was located separately and did not form a disulfide bond, and hydrogen bondings and π-π interaction were observed from the packing structure.

Keywords: X-ray crystal analysis; anthraquinone; artificial molecules; cysteine; mercapto group; packing structure; π-π interaction.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anthraquinones / chemical synthesis*
Crystallography, X-Ray
Cysteine / chemistry*
Disulfides / chemistry*
Hydrogen Bonding
Methionine / chemistry
Molecular Structure
Selenomethionine / chemistry
Sulfhydryl Reagents / chemistry

Substances

Anthraquinones
Disulfides
Sulfhydryl Reagents
Selenomethionine
Methionine
Cysteine