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Short Paper | Special issue | Vol 101, No. 1, 2020, pp.328-338
Published online, 30th July, 2019
DOI: 10.3987/COM-19-S(F)15
Synthesis of Axially Chiral Binaphthothiophene δ-Amino Acid Derivatives Bearing Chalcogen Bonds

Shohei Hamada, Shuo Wang, Takuya Murai, Yongning Xing, Takumi Inoue, Yoshihiro Ueda, Takahiro Sasamori, Takeo Kawabata, and Takumi Furuta*

*Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University, 1 Misasagi-Shichonocho, Yamashina, Kyoto 607-8412, Japan

Abstract

Axially chiral binaphthothiophene amino acid was synthesized as a stable artificial δ-amino acid. N- and C-protected derivatives of this unnatural amino acid were also prepared and applied for derivatization to the dipeptide. The crystal structure of the dipeptide revealed that the carbonyl groups of both the amide and the ester moieties were fixed with naphthothiophene rings in coplanar geometry via intramolecular chalcogen bonds.