Practical synthesis of natural plant-growth regulator 2-azahypoxanthine, its derivatives, and biotin-labeled probes

Kazutada Ikeuchi; Ryosuke Fujii; Shimpei Sugiyama; Tomohiro Asakawa; Makoto Inai; Yoshitaka Hamashima; Jae-Hoon Choi; Tomohiro Suzuki; Hirokazu Kawagishi; Toshiyuki Kan

doi:10.1039/C4OB00705K

Practical synthesis of natural plant-growth regulator 2-azahypoxanthine, its derivatives, and biotin-labeled probes†

Kazutada Ikeuchi,^a Ryosuke Fujii,^a Shimpei Sugiyama,^a Tomohiro Asakawa,^a Makoto Inai,^a Yoshitaka Hamashima,^a Jae-Hoon Choi,^b Tomohiro Suzuki,^b Hirokazu Kawagishi*^bcd and Toshiyuki Kan*^a

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^a School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan
E-mail: kant@u-shizuoka-ken.ac.jp
Fax: +81-54-264-5745
Tel: +81-54-264-5746

^b Research Institute of Green Science and Technology, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan
E-mail: achkawa@ipc.shizuoka.ac.jp
Fax: +81-54-238-4885
Tel: +81-54-238-4885

^c Graduate School of Science and Technology, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan

^d Graduate School of Agriculture, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan

Abstract

We describe a practical, large-scale synthesis of the “fairy-ring” plant-growth regulator 2-azahypoxanthine (AHX), and its biologically active hydroxyl metabolite (AOH) and riboside derivative (AHXr). AHXr, a biosynthetic intermediate, was synthesized from inosine via a biomimetic route. Biotinylated derivatives of AHX and AHXr were also synthesized as probes for mechanistic studies.

Organic & Biomolecular Chemistry

Practical synthesis of natural plant-growth regulator 2-azahypoxanthine, its derivatives, and biotin-labeled probes†

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Practical synthesis of natural plant-growth regulator 2-azahypoxanthine, its derivatives, and biotin-labeled probes

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