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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

. 2019 Mar ; 62 (3) : 118-125. [epub] 20190116

Language English Country England, Great Britain Media print-electronic

Document type Journal Article, Research Support, Non-U.S. Gov't

Grant support
IGA_LF_2018_032 Palacký University - International
IGA_PrF_2018_029 Palacký University - International
CZ.01.1.02/0.0/0.0/15_019/0004431 OP PIK - International
TE02000058 TAČR - International

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).

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