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Enzymatic glycosylation involving fluorinated carbohydrates

Enzymatic glycosylation involving fluorinated carbohydrates
Enzymatic glycosylation involving fluorinated carbohydrates
Fluorinated carbohydrates, where one (or more) fluorine atom(s) have been introduced into a carbohydrate structure, typically through deoxyfluorination chemistry, have a wide range of applications in the glycosciences. Fluorinated derivatives of galactose, glucose, N-acetylgalactosamine, N-acetylglucosamine, talose, fucose and sialic acid have been employed as either donor or acceptor substrates in glycosylation reactions. Fluorinated donors can be synthesised by synthetic methods or produced enzymatically from chemically fluorinated sugars. The latter process is mediated by enzymes such as kinases, phosphorylases and nucleotidyltransferases. Fluorinated donors produced by either method can subsequently be used in glycosylation reactions mediated by
glycosyltransferases, or phosphorylases yielding fluorinated oligosaccharide or glycoconjugate products. Fluorinated acceptor substrates are typically synthesised chemically. Glycosyltransferases are most commonly used in conjunction with natural donors to further elaborate fluorinated acceptor substrates. Glycoside hydrolases are used with either fluorinated donors or acceptors. The activity of enzymes towards fluorinated sugars is often lower than towards the natural sugar substrates irrespective of donor or acceptor. This may be in part attributed to elimination of the contribution of the hydroxyl group to the binding of the substrate to enzymes. However, in many cases, enzymes still maintain a significant activity, and reactions may be optimised
where necessary, enabling enzymes to be used more successfully in the production of fluorinated carbohydrates. This review describes the current state of the art regarding chemoenzymatic production of fluorinated carbohydrates, focusing specifically on examples of the enzymatic production of activated fluorinated donors and enzymatic glycosylation involving fluorinated sugars as either glycosyl donors or acceptors.
1477-0520
3423-3451
Council, Claire
d3b28ff6-e69a-4ec2-a4c8-99282a2609be
Kilpin, Kelly J.
303b34ac-6db0-43e5-b1de-89c89b293d0f
Gusthart, Jessica S
8a9a0071-e826-4ae7-ad7c-a9c0af737a23
Allman, Sarah A.
fbda335f-e4f2-44ca-8517-8aad42801f39
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Lee, Seung Seo
ee34fa26-5fb6-48c8-80c2-1f13ec4ccceb
Council, Claire
d3b28ff6-e69a-4ec2-a4c8-99282a2609be
Kilpin, Kelly J.
303b34ac-6db0-43e5-b1de-89c89b293d0f
Gusthart, Jessica S
8a9a0071-e826-4ae7-ad7c-a9c0af737a23
Allman, Sarah A.
fbda335f-e4f2-44ca-8517-8aad42801f39
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Lee, Seung Seo
ee34fa26-5fb6-48c8-80c2-1f13ec4ccceb

Council, Claire, Kilpin, Kelly J., Gusthart, Jessica S, Allman, Sarah A., Linclau, Bruno and Lee, Seung Seo (2020) Enzymatic glycosylation involving fluorinated carbohydrates. Organic & Biomolecular Chemistry, 18 (18), 3423-3451. (doi:10.1039/D0OB00436G).

Record type: Article

Abstract

Fluorinated carbohydrates, where one (or more) fluorine atom(s) have been introduced into a carbohydrate structure, typically through deoxyfluorination chemistry, have a wide range of applications in the glycosciences. Fluorinated derivatives of galactose, glucose, N-acetylgalactosamine, N-acetylglucosamine, talose, fucose and sialic acid have been employed as either donor or acceptor substrates in glycosylation reactions. Fluorinated donors can be synthesised by synthetic methods or produced enzymatically from chemically fluorinated sugars. The latter process is mediated by enzymes such as kinases, phosphorylases and nucleotidyltransferases. Fluorinated donors produced by either method can subsequently be used in glycosylation reactions mediated by
glycosyltransferases, or phosphorylases yielding fluorinated oligosaccharide or glycoconjugate products. Fluorinated acceptor substrates are typically synthesised chemically. Glycosyltransferases are most commonly used in conjunction with natural donors to further elaborate fluorinated acceptor substrates. Glycoside hydrolases are used with either fluorinated donors or acceptors. The activity of enzymes towards fluorinated sugars is often lower than towards the natural sugar substrates irrespective of donor or acceptor. This may be in part attributed to elimination of the contribution of the hydroxyl group to the binding of the substrate to enzymes. However, in many cases, enzymes still maintain a significant activity, and reactions may be optimised
where necessary, enabling enzymes to be used more successfully in the production of fluorinated carbohydrates. This review describes the current state of the art regarding chemoenzymatic production of fluorinated carbohydrates, focusing specifically on examples of the enzymatic production of activated fluorinated donors and enzymatic glycosylation involving fluorinated sugars as either glycosyl donors or acceptors.

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Accepted/In Press date: 16 April 2020
e-pub ahead of print date: 17 April 2020

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Local EPrints ID: 439629
URI: http://eprints.soton.ac.uk/id/eprint/439629
ISSN: 1477-0520
PURE UUID: 8ed45a64-a515-4459-b100-4c281616d137
ORCID for Claire Council: ORCID iD orcid.org/0000-0003-0600-4689
ORCID for Kelly J. Kilpin: ORCID iD orcid.org/0000-0001-8829-7213
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170
ORCID for Seung Seo Lee: ORCID iD orcid.org/0000-0002-8598-3303

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Date deposited: 28 Apr 2020 16:35
Last modified: 10 May 2022 04:01

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Contributors

Author: Claire Council ORCID iD
Author: Kelly J. Kilpin ORCID iD
Author: Jessica S Gusthart
Author: Sarah A. Allman
Author: Bruno Linclau ORCID iD
Author: Seung Seo Lee ORCID iD

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