ID 58589
Author
Takamura, Hiroyoshi Department of Biological Science, Graduate School of Natural Science and Technology, Okayama University ORCID Kaken ID publons researchmap
Motose, Hiroyasu Graduate School of Natural Science and Technology, Okayama University ORCID Kaken ID publons researchmap
Otsu, Taichi Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University
Shinohara, Shiori Department of Biological Science, Graduate School of Natural Science and Technology, Okayama University
Kouno, Ryugo Department of Biological Science, Graduate School of Natural Science and Technology, Okayama University
Kadota, Isao Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University Kaken ID publons researchmap
Takahashi, Taku Department of Biological Science, Graduate School of Natural Science and Technology, Okayama University ORCID Kaken ID researchmap
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
Amines
Biological activity
Chemical synthesis
Reductive amination
Structure‐activity relationships
Note
This fulltext is available in Mar. 2021.
Published Date
2020-03-20
Publication Title
European Journal of Organic Chemistry
Publisher
Wiley
ISSN
1434193X
NCID
AA1118165X
Content Type
Journal Article
language
英語
OAI-PMH Set
岡山大学
File Version
author
DOI
Web of Science KeyUT
Related Url
https://doi.org/10.1002/ejoc.202000322
Funder Name
Ministry of Education, Culture, Sports, Science and Technology
助成番号
17K05862
16H01245
19K06724