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Enzymatic glycosylation involving fluorinated carbohydrates

(2020) ORGANIC & BIOMOLECULAR CHEMISTRY. 18(18). p.3423-3451
Author
Organization
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.
Keywords
MONOPHOSPHATE-SIALIC-ACID, CHEMOENZYMATIC SYNTHESIS, MECHANISTIC PROBES, SUGAR NUCLEOTIDE, TRANS-SIALIDASE, ONE-POT, SUBSTRATE, ANALOGS, SPECIFICITY, ACCEPTOR

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MLA
Council, Claire E., et al. “Enzymatic Glycosylation Involving Fluorinated Carbohydrates.” ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 18, no. 18, 2020, pp. 3423–51, doi:10.1039/d0ob00436g.
APA
Council, C. E., Kilpin, K. J., Gusthart, J. S., Allman, S. A., Linclau, B., & Lee, S. S. (2020). Enzymatic glycosylation involving fluorinated carbohydrates. ORGANIC & BIOMOLECULAR CHEMISTRY, 18(18), 3423–3451. https://doi.org/10.1039/d0ob00436g
Chicago author-date
Council, Claire E., Kelly J. Kilpin, Jessica S. Gusthart, Sarah A. Allman, Bruno Linclau, and Seung Seo Lee. 2020. “Enzymatic Glycosylation Involving Fluorinated Carbohydrates.” ORGANIC & BIOMOLECULAR CHEMISTRY 18 (18): 3423–51. https://doi.org/10.1039/d0ob00436g.
Chicago author-date (all authors)
Council, Claire E., Kelly J. Kilpin, Jessica S. Gusthart, Sarah A. Allman, Bruno Linclau, and Seung Seo Lee. 2020. “Enzymatic Glycosylation Involving Fluorinated Carbohydrates.” ORGANIC & BIOMOLECULAR CHEMISTRY 18 (18): 3423–3451. doi:10.1039/d0ob00436g.
Vancouver
1.
Council CE, Kilpin KJ, Gusthart JS, Allman SA, Linclau B, Lee SS. Enzymatic glycosylation involving fluorinated carbohydrates. ORGANIC & BIOMOLECULAR CHEMISTRY. 2020;18(18):3423–51.
IEEE
[1]
C. E. Council, K. J. Kilpin, J. S. Gusthart, S. A. Allman, B. Linclau, and S. S. Lee, “Enzymatic glycosylation involving fluorinated carbohydrates,” ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 18, no. 18, pp. 3423–3451, 2020.
@article{01GMMX7784DC6XJNHWA56DTA3W,
  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.}},
  author       = {{Council, Claire E. and  Kilpin, Kelly J. and  Gusthart, Jessica S. and  Allman, Sarah A. and Linclau, Bruno and  Lee, Seung Seo}},
  issn         = {{1477-0520}},
  journal      = {{ORGANIC & BIOMOLECULAR CHEMISTRY}},
  keywords     = {{MONOPHOSPHATE-SIALIC-ACID,CHEMOENZYMATIC SYNTHESIS,MECHANISTIC PROBES,SUGAR NUCLEOTIDE,TRANS-SIALIDASE,ONE-POT,SUBSTRATE,ANALOGS,SPECIFICITY,ACCEPTOR}},
  language     = {{eng}},
  number       = {{18}},
  pages        = {{3423--3451}},
  title        = {{Enzymatic glycosylation involving fluorinated carbohydrates}},
  url          = {{http://doi.org/10.1039/d0ob00436g}},
  volume       = {{18}},
  year         = {{2020}},
}

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