Dimitriou, E and Miller, GJ (2019) Exploring a glycosylation methodology for the synthesis of hydroxamate-modified alginate building blocks. Organic & Biomolecular Chemistry, 17 (42). pp. 9321-9335. ISSN 1477-0520

[thumbnail of Manuscript_Dimitriou_Resubmission.docx] Text
Manuscript_Dimitriou_Resubmission.docx - Accepted Version
Available under License Creative Commons Attribution Non-commercial.

Download (735kB)


Alginate, an anionic polysaccharide, is an important industrial biomaterial naturally harvested from seaweed. Many of its important physicochemical properties derive from the presence of charged carboxylate groups presented as uronic acids within the polysaccharide backbone. An ability to modify these carboxylates with alternate functional groups would enable the design and implementation of new alginate systems possessing different physicochemical properties. We present herein our approach to the chemical synthesis of alginate disaccharides, modified at the carboxylate C6 position with bioisosteric hydroxamate residues. The synthesis and utilisation of C6-hydroxamate donor and acceptor building blocks enables a first access to protected α- and β-linked hydroxamate-containing disaccharides, additionally equipped with a functional tether at the reducing terminus. The evaluation of these building blocks for chemical glycosylation demonstrates the incorporation of bioisosteric functional groups into an alginate disaccharide backbone and highlights the important contribution of both acceptor and donor reactivity underpinning uronate-level glycosylations.

Item Type: Article
Additional Information: This is the accepted author manuscript (AAM). The final published version (version of record) is available online via Royal Society of Chemistry at http://doi.org/10.1039/c9ob02053e - please refer to any applicable terms of use of the publisher.
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Natural Sciences > School of Chemical and Physical Sciences
Depositing User: Symplectic
Date Deposited: 10 Oct 2019 10:30
Last Modified: 04 Oct 2020 01:30
URI: https://eprints.keele.ac.uk/id/eprint/7004

Actions (login required)

View Item
View Item