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Chemical Synthesis and Biological Effect on Xylem Formation of Xylemin and Its Analogues

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Xylemin (6 ) and its designed structural analogues 18 –23 , N ‐(4‐aminobutyl)alkylamines, were synthesized by 2‐nitrobenzenesulfonamide (Ns) strategy. Investigation of the improved synthesis of 20 –23 resulted in the… Click to show full abstract

Xylemin (6 ) and its designed structural analogues 18 –23 , N ‐(4‐aminobutyl)alkylamines, were synthesized by 2‐nitrobenzenesulfonamide (Ns) strategy. Investigation of the improved synthesis of 20 –23 resulted 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 analogue N ‐(4‐aminobutyl)cyclopentylamine (21 ) promoted the expression level of thermospermine synthase ACAULIS5 (ACL5 ) and enhanced xylem formation. In addition, xylemin (6 ) was found to significantly promote lateral root formation, whereas xylemin analogues 18 –23 including 21 did not. These results indicate that the analogue 21 has the potential as a novel inhibitor of thermospermine synthesis to work specifically in xylem differentiation.

Keywords: xylem formation; xylemin analogues; synthesis; xylemin

Journal Title: European Journal of Organic Chemistry
Year Published: 2020

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