Abstract
The phloem sucrose transporter, AtSUC2, is promiscuous with respect to substrate recognition, transporting a range of glucosides in addition to sucrose, including naturally occurring coumarin glucosides. We used the inherent fluorescence of coumarin glucosides to probe the specificity of AtSUC2 for its substrates, and determined the structure-activity relationships that confer phloem transport in vivo using Arabidopsis seedlings. In addition to natural coumarin glucosides, we synthesized new compounds to identify key structural features that specify recognition by AtSUC2. Our analysis of the structure-activity relationship revealed that the presence of a free hydroxyl group on the coumarin moiety is essential for binding by AtSUC2 and subsequent phloem mobility. Structural modeling of the AtSUC2 substrate-binding pocket explains some important structural requirements for the interaction of coumarin glucosides with the AtSUC2 transporter.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 2473-2482 |
| Number of pages | 10 |
| Journal | Journal of experimental botany |
| Volume | 69 |
| Issue number | 10 |
| DOIs | |
| State | Published - Apr 27 2018 |
Bibliographical note
Funding Information:The authors acknowledge funding from the Biotechnology and Biological Sciences Research Council (BB/M025160/1), the Division of Chemical Sciences, Geosciences, and Biosciences, and Office of Basic Energy Sciences of the U.S. Department of Energy (DE-FG02-10ER15886), and thank Dr Tim Hawkes and Dr Ryan Ramsey (Syngenta) for numerous helpful discussions.
Publisher Copyright:
© The Author(s) 2018. Published by Oxford University Press on behalf of the Society for Experimental Biology.
Keywords
- Arabidopsis
- coumarin
- fluorescence
- glucosides
- imaging
- phloem
- sucrose
- transporters