Synthesis and inhibitory activity of deoxy-d-allose amide derivative against plant growth

Md Tazul Islam Chowdhury; Hikaru Ando; Ryo C Yanagita; Yasuhiro Kawanami

doi:10.1080/09168451.2018.1445521

Synthesis and inhibitory activity of deoxy-d-allose amide derivative against plant growth

Biosci Biotechnol Biochem. 2018 May;82(5):775-779. doi: 10.1080/09168451.2018.1445521. Epub 2018 Mar 7.

Authors

Md Tazul Islam Chowdhury¹, Hikaru Ando², Ryo C Yanagita², Yasuhiro Kawanami²

Affiliations

¹ Division of Applied Bioresource Science, The United Graduate School of Agricultural Sciences, Ehime University, Matsuyama, Japan.
² Faculty of Agriculture, Kagawa University, Miki-cho, Japan.

PMID: 29513080
DOI: 10.1080/09168451.2018.1445521

Abstract

1,2,6-Trideoxy-6-amido-d-allose derivative was synthesized and found to exhibit higher growth-inhibitory activity against plants than the corresponding deoxy-d-allose ester, which indicates that an amide group at C-6 of the deoxy-d-allose amide enhances inhibitory activity. In addition, the mode of action of the deoxy-d-allose amide was significantly different from that of d-allose which inhibits gibberellin signaling. Co-addition of gibberellin GA₃ restored the growth of rice seedlings inhibited by the deoxy-d-allose amide, suggesting that it might inhibit biosynthesis of gibberellins in plants to induce growth inhibition.

Keywords: DMF: N,N-dimethylformamide; GA: gibberellin; Rare sugar; TsCl: 4-toluenesulfonyl chloride; d-allose; gibberellin biosynthesis; inhibitory activity.