Purines. LV. Syntheses and cytokinin activities of some adenine and adenosine derivatives related to 1'-methylzeatin

Article abstract of DOI:10.1248/cpb.41.1362

(1'S)-1'-Methyl-cis-zeatin [(1'S)-2] and its 9-β-D-ribofuranoside [(1'S)- 4] were synthesized from L-alanine through [S-(Z)]-4-amino-2-methyl-2- penten-1-ol ethanedioate [(S)-3]. Condensations of 2-hydroxy-6- methylthiopurine (16) with the trans-isomeric amine salt [(S)-15], its enantiomer [(R)-15], and the racemic modification [(±)-15] furnished (1'S)- , (1'R)-, and (±)-2-hydroxyl-1'-methyl-trans-zeatins (6), respectively. A similar condensation of 16 with methylamine yielded 2-hydroxy-N⁶- methyladenine (7). These adenine derivatives were tested for cytokinin activity in the tobacco callus bioassay, and the order of their activity was (1'R)-6>(±)-6>(1'S)-2>7; on the other hand, (1''S)-4 and (1'S)-6 were completely inactive at 0.1-100 μM and 0.01-10 μM concentrations, respectively. As a result of the above syntheses of (1'R)-6, (1'S)-6, (±)- 6, and 7, the gross structures of a marine green alga cytokinin and of a blue coral cytokinin were established to be 6 and 7, respectively.

Full text of DOI:10.1248/cpb.41.1362

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