title: Practical synthesis of natural plant-growth regulator 2-azahypoxanthine, its derivatives, and biotin-labeled probes.
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.
authors.affiliation: School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan. kant@u-shizuoka-ken.ac.jp.
authors.forename: Kazutada
authors.initials: K
authors.lastname: Ikeuchi
authors.forename: Ryosuke
authors.initials: R
authors.lastname: Fujii
authors.forename: Shimpei
authors.initials: S
authors.lastname: Sugiyama
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Asakawa
authors.forename: Makoto
authors.initials: M
authors.lastname: Inai
authors.forename: Yoshitaka
authors.initials: Y
authors.lastname: Hamashima
authors.forename: Jae-Hoon
authors.initials: JH
authors.lastname: Choi
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Suzuki
authors.forename: Hirokazu
authors.initials: H
authors.lastname: Kawagishi
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Kan
mesh_terms: D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D001710:Biotin / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods*; D007042:Hypoxanthines / Q000138:chemical synthesis* / Q000737:chemistry; D010937:Plant Growth Regulators / Q000138:chemical synthesis* / Q000737:chemistry; D013194:Staining and Labeling
chemical_list: D000480:Alkynes; D001386:Azides; D007042:Hypoxanthines; D010937:Plant Growth Regulators; D001710:Biotin; C012759:2-azahypoxanthine