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

Hiroyoshi Takamura, Hiroyasu Motose, Taichi Otsu, Shiori Shinohara, Ryugo Kouno, Isao Kadota, Taku Takahashi

Research output: Contribution to journalArticle

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.

Original languageEnglish
Pages (from-to)2745-2753
Number of pages9
JournalEuropean Journal of Organic Chemistry
Volume2020
Issue number18
DOIs
Publication statusPublished - May 14 2020

Keywords

  • Amines
  • Biological activity
  • Chemical synthesis
  • Reductive amination
  • Structure-activity relationships

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Chemical Synthesis and Biological Effect on Xylem Formation of Xylemin and Its Analogues'. Together they form a unique fingerprint.

  • Cite this