Chemical synthesis of amphiphilic glycoconjugates: Access to amino, fluorinated and sulfhydryl oleyl glucosides.

Porter, Jack; Parisi, Daniele; Miller, Timothy; Cheallaigh, Aisling Ní; Miller, Gavin J

Abstract

Amphiphilic glycoconjugates offer an important prospect for development as chemical biology tools and biosurfactants. The chemical synthesis of such materials is required to expedite such prospect, compounded by the example of oleyl glycosides. Herein, we report a mild and reliable glycosylation method to access oleyl glucosides, glycosidating oleyl alcohol with α-trichloroacetimidate donors. We demonstrate capability for this methodology, extending it to synthesise the first examples of pyranose-component fluorination and sulfhydryl modifications within glucosides and glucosamines of oleyl alcohol. These compounds provide an exciting series of tools to explore processes and materials that utilise oleyl glycosides, including as probes for glycosphingolipid metabolism. [Abstract copyright: Copyright © 2023 The Author(s). Published by Elsevier Ltd.. All rights reserved.]

Citation

Porter, J., Parisi, D., Miller, T., Cheallaigh, A. N., & Miller, G. J. (2023). Chemical synthesis of amphiphilic glycoconjugates: Access to amino, fluorinated and sulfhydryl oleyl glucosides. Carbohydrate Research, 530, Article 108854. https://doi.org/10.1016/j.carres.2023.108854

• Journal Article Type: Article
• Acceptance Date: May 23, 2023
• Online Publication Date: May 30, 2023
• Publication Date: 2023-08
• Deposit Date: Jul 11, 2023
• Journal: Carbohydrate research
• Print ISSN: 0008-6215
• Electronic ISSN: 1873-426X
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 530
• Article Number: 108854
• DOI: https://doi.org/10.1016/j.carres.2023.108854
• Keywords: Glycosides - chemistry, Glycoconjugates - chemistry, Glucosides, Fatty Alcohols, Sulfhydryl Compounds