The synthesis and glycoside formation of polyfluorinated carbohydrates
The synthesis and glycoside formation of polyfluorinated carbohydrates
Fluorinated carbohydrates have found many applications in the glycosciences. Typically, these contain fluorination at a single position. There are not many applications involving polyfluorinated carbohydrates, here defined as monosaccharides in which more than one carbon has at least one fluorine substituent directly attached to it, with the notable exception of their use as mechanism-based inhibitors. The increasing attention to carbohydrate physical properties, especially around lipophilicity, has resulted in a surge of interest for this class of compounds. This review covers the considerable body of work toward the synthesis of polyfluorinated hexoses, pentoses, ketosugars, and aminosugars including sialic acids and nucleosides. An overview of the current state of the art of their glycosidation is also provided.
15503-15602
Huonnic, Kler
095e77fd-6ce1-49df-94c3-584e25a4f2f2
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
25 May 2022
Huonnic, Kler
095e77fd-6ce1-49df-94c3-584e25a4f2f2
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Huonnic, Kler and Linclau, Bruno
(2022)
The synthesis and glycoside formation of polyfluorinated carbohydrates.
Chemical Reviews, 122 (20), .
(doi:10.1021/acs.chemrev.2c00086).
Abstract
Fluorinated carbohydrates have found many applications in the glycosciences. Typically, these contain fluorination at a single position. There are not many applications involving polyfluorinated carbohydrates, here defined as monosaccharides in which more than one carbon has at least one fluorine substituent directly attached to it, with the notable exception of their use as mechanism-based inhibitors. The increasing attention to carbohydrate physical properties, especially around lipophilicity, has resulted in a surge of interest for this class of compounds. This review covers the considerable body of work toward the synthesis of polyfluorinated hexoses, pentoses, ketosugars, and aminosugars including sialic acids and nucleosides. An overview of the current state of the art of their glycosidation is also provided.
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Linclau manuscript revised 2_plain text_acc
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acs.chemrev.2c00086
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Accepted/In Press date: 6 May 2022
e-pub ahead of print date: 25 May 2022
Published date: 25 May 2022
Additional Information:
Funding Information:
K.H. and B.L. thank the University of Southampton for funding, and B.L. acknowledges Ghent University and the Research Foundation Flanders (FWO, Belgium) for an Odysseus Type I grant (G0F5621N).
Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.
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Local EPrints ID: 457600
URI: http://eprints.soton.ac.uk/id/eprint/457600
ISSN: 0009-2665
PURE UUID: cb93b5f6-5af7-4800-9365-017c552be304
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Date deposited: 13 Jun 2022 16:59
Last modified: 17 Mar 2024 03:56
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Author:
Kler Huonnic
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