Syntheses of cis-Zeatin and Its 9-(2-Deoxy-β-D-ribofuranosyl) Derivative : A Novel Synthetic Route to the Side Chain at C(6), and Cytokinin Activity

Antonio EVIDENTE; Gennaro PICCIALLI; Angelo SISTO; Masashi OHBA; Kei HONDA; Tozo FUJII

doi:10.1248/cpb.40.1937

/, / 大場正志, 本田圭, 藤井澄三, Kei HONDA, Tozo FUJII

著者情報

キーワード: cis-zeatin synthesis, cis-zeatin 9-(2-deoxy-β-D-ribofuranosyl), trans-zeatin 9-β-D-ribofuranosyl, trans-zeatin 9-(2-deoxy-β-D-ribofuranosyl), glycine, α-amino aldehyde olefination, Z stereoselectivity, diisobutylaluminum hydride reduction, cytokinin activity, chlorophyll biosynthesis stimulation

ジャーナルフリー

1992 年 40 巻 7 号 p. 1937-1939

DOI https://doi.org/10.1248/cpb.40.1937

詳細

抄録

cis-Zeatin (3a) and its 9-(2-deoxy-β-D-ribofuranosyl) derivative (3c) have been synthesized from N-[(1, 1-dimethylethoxy)carbonyl]glycine methyl ester (5) in 5 steps by adopting the "α-amino aldehyde/olefination" technology. The new cis-zeatin derivative (3c), its trans isomer (1c), and known trans-zeatin 9-β-D-riboside (1b) were tested for cytokinin activity in the stimulation of chlorophyll biosynthesis in etiolated cucumber cotyledons. The riboside 1b turned out to be the most active cytokinin among them, while the deoxyribosides 1c and 3c showed a marked decrease and a total loss, respectively, of cytokinin activity.

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