Tools
Tools
Hems, Edward S., Nepogodiev, Sergey A., Rejzek, Martin and Field, Robert A. 
ORCID: https://orcid.org/0000-0001-8574-0275
(2018)
Synthesis of glyceryl glycosides related to A-type prymnesin toxins.
Carbohydrate Research, 463.
pp. 14-23.
ISSN 0008-6215
Abstract
A suite of glycosylated glycerol derivatives representing various fragments of the glycosylated ichthyotoxins called prymnesins were chemically synthesised. Glycerol was used to represent a small fragment of the prymnesin backbone, and was glycosylated at the 2° position with the sugars currently reported to be present on prymnesin toxins. Neighbouring group participation was utilised to synthesise 1,2-trans-glycosides. SnCl2-promoted glycosylation with furanosyl fluorides gave 1,2-cis-furanosides with moderate stereocontrol, whilst TMSOTf promoted glycosylation with a furanosyl imidate gave a 1,2-cis-furanoside with good stereocontrol. The chemical synthesis of two larger glyceryl diglycoside fragments of prymnesin-1, glycosylated with α-ʟ-arabinopyranose and α-ᴅ-ribofuranose, is also described. As the stereochemistry of the prymnesin backbones at this region is undefined, both the 2R- and 2S- glycerol isomers were synthesised. The separated diastereoisomers were distinguished by comparing NOESY NMR with computational models.
| Item Type: | Article |
|---|---|
| Additional Information: | Funding Information: These studies were supported in the UK by BBSRC Institute Strategic Programme on Understanding and Exploiting Metabolism [BB/J004561/1] and the John Innes Foundation. We thank Gerhard Saalbach for his assistance with recording HRMS spectra. MarvinSketch was used for displaying lowest energy calculation 3D models, and Calculator Plugins were used for structure property prediction and calculation. Marvin 15.1.19.0, 2015, ChemAxon (http://www.chemaxon.com). Publisher Copyright: © 2018 The Authors |
| Uncontrolled Keywords: | algae,glyceryl glycosides,prymnesins,prymnesium parvum,toxins,analytical chemistry,biochemistry,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1600/1602 |
| Faculty \ School: | Faculty of Science > School of Chemistry, Pharmacy and Pharmacology |
| Related URLs: | |
| Depositing User: | LivePure Connector |
| Date Deposited: | 04 Sep 2024 08:33 |
| Last Modified: | 25 Sep 2024 18:06 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/96504 |
| DOI: | 10.1016/j.carres.2018.04.008 |
Actions (login required)
 |
View Item |