Synthesis of [15 N4 ] purine labeled cytokinin glycosides derived from zeatins and topolins with 9-β-d, 7-β-d-glucopyranosyl, or 9-β-d-ribofuranosyl group

Abstract

Synthesis of [¹⁵ N₄ ] purine labeled cytokinine glycosides derived from zeatins and topolins containing a 9-β-d, 7-β-d-glucopyranosyl, or 9-β-d-ribofuranosyl group is described. These N⁶ -substituted adenine derivatives are intended as internal analytic standards for phytohormone analysis. All labeled compounds were prepared from 6-chloro[¹⁵ N₄ ]purine (1). The equilibrium reaction of 1 with acetobromo-α-d-glucose gave isomeric 7-β-d (3) and 9-β-d (4) chloro glucosyl precursors, which were treated with the corresponding amines to get desired labeled cytokinin 7-β-d (6) and 9-β-d (5) glucopyranosides. Cytokinins containing 9-β-d-ribofuranosyl group (8) were obtained by direct enzymatic transglycosylation reaction of cytokinins (7) prepared from 6-chloro[¹⁵ N₄ ] purine (1).

Keywords: cytokinins; internal standard; labeled adenine; labeled purine; topolin; zeatin.