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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,Toshiyuki Kan
Organic & Biomolecular Chemistry Pub Date : 04/14/2014 00:00:00 , DOI:10.1039/C4OB00705K
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.

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