Syntheses and absolute configurations of the cytokinins 1′-methylzeatin and its 9-riboside

✍ Scribed by Taisuke Itaya; Tozo Fujii; Antonio Evidente; Giacomino Randazzo; Giuseppe Surico; Nicola S. Iacobellis

• Book ID: 104221216
• Publisher: Elsevier Science
• Year: 1986
• Tongue: French
• Weight: 233 KB
• Volume: 27
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)87806-5

✦ Synopsis

On the basis of the chiral syntheses of (l'R)-I and (l's)-1 and of their 9-ribosides (1"R)-III and (l"S)-III from n-and L-alanines, the structures of the cytokinins l'-methylzeatin and its 9-riboside have been established to be (l'R)-I and (1"R)-m. In quite recent papers, 1J some of us reported the isolation of two new cytokinins from the culture filtrate of Pseudomonas syringae pv. savastanoi and proposed the gross structures I 1 and III 2 for them on the basis of spectroscopic data and comparison with related adenine derivatives including the known cytokinins 3 zeatin (II) and its 9-riboside (IV). The new cytokinins, l'-methylzeatin (I) and its 9-B-D-ribofuranosyl derivative (IX), are unique in that their N6-substituents consist of a branched ally1 alcoholic Cg unit with an asymmetric asymmetric cation, we assignment kinins.

R; R2