Chemical synthesis and biological effect on xylem formation of xylemin and Its analogues
Chemical synthesis and biological effect on xylem formation of xylemin and Its analogues
复制标题
xylemin及其类似物的化学合成及其对木质部形成的生物效应
DOI：
10.1002/ejoc.202000322
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发表时间：
2020
期刊：
影响因子：
--
通讯作者：
Taku Takahashi
中科院分区：
文献类型：
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作者：
Hiroyoshi Takamura;Hiroyasu Motose;Taichi Otsu;Shiori Shinohara;Ryugo Kouno;Isao Kadota;Taku Takahashi
用2-硝基苯磺酰胺(NS)策略合成了木素(6)及其设计的结构类似物18-23，N-(4-氨基丁基)烷基胺。对改进的20-23的合成进行了研究，从商业上可获得的相应的酮开发了这些类似物的一步合成。对合成分子的生物学评价表明，木素(6)和类似物N-(4-氨基丁基)环戊胺(21)促进了温度敏合酶ACAULIS5(ACL5)的表达，促进了木质部的形成。此外，木素(6)对侧根的形成有显著的促进作用，而木素类似物18-23(包括21)则没有促进侧根形成的作用。这些结果表明，类似物21有可能成为一种新型的热敏胺合成抑制剂，在木质部分化中具有特异性作用。
Xylemin (6) and its designed structural analogues18–23,N‐(4‐aminobutyl)alkylamines, were synthesized by 2‐nitrobenzenesulfonamide (Ns) strategy. Investigation of the improved synthesis of20–23resulted in the development of one‐step synthesis of these analogues from the commercially available corresponding ketones. Biological assessment of the synthetic molecules elucidated that xylemin (6) and the analogueN‐(4‐aminobutyl)cyclopentylamine (21) promoted the expression level of thermospermine synthaseACAULIS5(ACL5) and enhanced xylem formation. In addition, xylemin (6) was found to significantly promote lateral root formation, whereas xylemin analogues18–23including21did not. These results indicate that the analogue21has the potential as a novel inhibitor of thermospermine synthesis to work specifically in xylem differentiation.