| ID | 58589 |
| FullText URL | |
| Author |
Takamura, Hiroyoshi
Department of Biological Science, Graduate School of Natural Science and Technology, Okayama University
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Motose, Hiroyasu
Graduate School of Natural Science and Technology, Okayama University
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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
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Takahashi, Taku
Department of Biological Science, Graduate School of Natural Science and Technology, Okayama University
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| 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.
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| Keywords | Amines
Biological activity
Chemical synthesis
Reductive amination
Structure‐activity relationships
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| Note | This fulltext is available in Mar. 2021.
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| Published Date | 2020-03-20
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| Publication Title |
European Journal of Organic Chemistry
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| Volume | volume2020
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| Issue | issue18
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| Publisher | Wiley
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| Start Page | 2745
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| End Page | 2753
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| ISSN | 1434193X
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| NCID | AA1118165X
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| Content Type |
Journal Article
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| language |
English
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| OAI-PMH Set |
岡山大学
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| File Version | author
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| DOI | |
| Web of Science KeyUT | |
| Related Url | https://doi.org/10.1002/ejoc.202000322
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| Funder Name |
Ministry of Education, Culture, Sports, Science and Technology
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| 助成番号 | 17K05862
16H01245
19K06724
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