3-Nitro-2-pyridinesulfenyl-mediated solid-phase disulfide ligation in the synthesis of disulfide bond-containing cyclic peptides

Akihiro Taguchi; Kentarou Fukumoto; Yuya Asahina; Akihiro Kajiyama; Shunsuke Shimura; Keisuke Hamada; Kentaro Takayama; Fumika Yakushiji; Hironobu Hojo; Yoshio Hayashi

doi:10.1039/C5OB00030K

3-Nitro-2-pyridinesulfenyl-mediated solid-phase disulfide ligation in the synthesis of disulfide bond-containing cyclic peptides†

Akihiro Taguchi,‡^a Kentarou Fukumoto,‡^b Yuya Asahina,^c Akihiro Kajiyama,^a Shunsuke Shimura,^a Keisuke Hamada,^a Kentaro Takayama,^a Fumika Yakushiji,^a Hironobu Hojo^c and Yoshio Hayashi*^a

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^a Department of Medicinal Chemistry, School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
E-mail: yhayashi@toyaku.ac.jp

^b Kokusan Chemical Co., Ltd, 3-1-3 Nihonbashihoncho, Chuo-ku, Tokyo 103-0023, Japan

^c Laboratory of Protein Organic Chemistry, Institute for Protein Research, Osaka University, 3-2 Yamadaoka, Suita, Osaka 565-0871, Japan

Abstract

A new solid-phase disulfide ligation method is developed to prepare a disulfide peptide from two types of Cys-containing peptide fragments with minimum purification steps. In combination with the subsequent intramolecular amide bond formation, a cyclic nonapeptide, oxytocin, was efficiently synthesized as a fundamental model for more complex cyclic peptides.

Organic & Biomolecular Chemistry

3-Nitro-2-pyridinesulfenyl-mediated solid-phase disulfide ligation in the synthesis of disulfide bond-containing cyclic peptides†

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3-Nitro-2-pyridinesulfenyl-mediated solid-phase disulfide ligation in the synthesis of disulfide bond-containing cyclic peptides

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