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

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

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. B...

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Veröffentlicht in:Organic & biomolecular chemistry 2014-06, Vol.12 (23), p.3813-3815
Hauptverfasser: Ikeuchi, Kazutada, Fujii, Ryosuke, Sugiyama, Shimpei, Asakawa, Tomohiro, Inai, Makoto, Hamashima, Yoshitaka, Choi, Jae-Hoon, Suzuki, Tomohiro, Kawagishi, Hirokazu, Kan, Toshiyuki
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes - chemistry
Azides - chemistry
Biotin - chemistry
Chemistry, Organic - methods
Hypoxanthines - chemical synthesis
Hypoxanthines - chemistry
Plant Growth Regulators - chemical synthesis
Plant Growth Regulators - chemistry
Staining and Labeling
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Zusammenfassung: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c4ob00705k