Purines. XXXIII. Syntheses and Cytokinin Activities of Both Enantiomers of 1'-Methylzeatin and Their 9-β-D-Ribofuranosides

• FUJII T.

  Faculty of Pharmaceutical Sciences, Kanazawa University

• ITAYA Taisuke

  Faculty of Pharmaceutical Sciences, Kanazawa University

• MATSUBARA Satoshi

  Japan and Laboratory of Applied Biology, Kyoto Prefectural University

Abstract

The structures and absolute configurations of the cytokinins 1'-methylzeatin and its 9-riboside, both secreted by Pseudomonas syringae pv savastanoi, have been established as [R-(E)]-2-methyl-4-(9H-purin-6-ylamino)-2-penten-1-ol[(1'R)-2] and [R-(E)]-N-(4-hydroxy-1,3-dimethyl-2-butenyl)adenosine [(1''R)-4], respectively, as a result of the chiral syntheses of (1'R)- and (1'S)-1'-methylzeatins [(1'R)-2 and (1'S)-2] and of their 9-β-D-ribofuranosides [(1''R)-4 and (1''S)-4] from D- and L-alanines. These zeatin derivatives were tested for cytokinin activity in the tobacco callus and the lettuce seed germination bioassays. The "natural" enantiomer (1'R)-2 was found to be as active as zeatin (1) itself and more active than its 9-riboside [(1''R)-4]. The "unnatural" enantiomer (1'S)-2 and its 9-riboside [(1''S)-4] were less active than the corresponding natural cytokinins, (1'R)-2 and (1''R)-4,respectively.

Journal

• Chem. Pharm. Bull.

  Chem. Pharm. Bull. 37 1758-1763, 1989

  The Pharmaceutical Society of Japan

Keywords

• 1'-methylzeatin
• 1'-methylzeatin 9-riboside
• chiral synthesis
• alanine
• Wittig reaction
• α, β-unsaturated ester
• cytokinin activity
• ^1H-NMR
• ^<13>C-NMR
• CD

Details

• CRID: 1571980077391616640
• NII Article ID: 110003627853
• NII Book ID: AA00602100
• ISSN: 00092363
• Text Lang: en
• Data Source:
  • CiNii Articles