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

Synthesis of [15N4] 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[15N4]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[15N4] purine (1). Synthesis and characterization of some [15N4] purine labeled cytokinin glycosides derived from zeatins and topolins containing 9‐β‐d, 7‐β‐d‐glucopyranosyl, or 9‐β‐d‐ribofuranosyl group with using chemical and enzymatic approaches is described. [ABSTRACT FROM AUTHOR]