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Profiling Substrate Promiscuity of Wild-Type Sugar Kinases for Multi-fluorinated Monosaccharides.

Keenan T, Parmeggiani F, Malassis J, Fontenelle CQ, Vendeville JB, Offen W, Both P, Huang K, Marchesi A, Heyam A, Young C, Charnock SJ, Davies GJ, Linclau B, Flitsch SL, Fascione MA
Cell Chem Biol 27 1199-1206.e5 (2020)
Related entries: 6teq, 6ter

Cited: 7 times
EuropePMC logo PMID: 32619452

Abstract

Fluorinated sugar-1-phosphates are of emerging importance as intermediates in the chemical and biocatalytic synthesis of modified oligosaccharides, as well as probes for chemical biology. Here we present a systematic study of the activity of a wide range of anomeric sugar kinases (galacto- and N-acetylhexosamine kinases) against a panel of fluorinated monosaccharides, leading to the first examples of polyfluorinated substrates accepted by this class of enzymes. We have discovered four new N-acetylhexosamine kinases with a different substrate scope, thus expanding the number of homologs available in this subclass of kinases. Lastly, we have solved the crystal structure of a galactokinase in complex with 2-deoxy-2-fluorogalactose, giving insight into changes in the active site that may account for the specificity of the enzyme toward certain substrate analogs.

Reviews citing this publication (1)

  1. Biocatalytic Approaches to Building Blocks for Enzymatic and Chemical Glycan Synthesis. Dolan JP, Cosgrove SC, Miller GJ. JACS Au 3 47-61 (2023)

Articles citing this publication (6)

  1. Automated Glycan Assembly of 19 F-labeled Glycan Probes Enables High-Throughput NMR Studies of Protein-Glycan Interactions. Fittolani G, Shanina E, Guberman M, Seeberger PH, Rademacher C, Delbianco M. Angew Chem Int Ed Engl 60 13302-13309 (2021)
  2. Cell-specific bioorthogonal tagging of glycoproteins. Cioce A, Calle B, Rizou T, Lowery SC, Bridgeman VL, Mahoney KE, Marchesi A, Bineva-Todd G, Flynn H, Li Z, Tastan OY, Roustan C, Soro-Barrio P, Rafiee MR, Garza-Garcia A, Antonopoulos A, Wood TM, Keenan T, Both P, Huang K, Parmeggian F, Snijders AP, Skehel M, Kjær S, Fascione MA, Bertozzi CR, Haslam SM, Flitsch SL, Malaker SA, Malanchi I, Schumann B. Nat Commun 13 6237 (2022)
  3. Rapid Screening of Diverse Biotransformations for Enzyme Evolution. Kempa EE, Galman JL, Parmeggiani F, Marshall JR, Malassis J, Fontenelle CQ, Vendeville JB, Linclau B, Charnock SJ, Flitsch SL, Turner NJ, Barran PE. JACS Au 1 508-516 (2021)
  4. Obtaining Pure 1H NMR Spectra of Individual Pyranose and Furanose Anomers of Reducing Deoxyfluorinated Sugars. Poškaitė G, Wheatley DE, Wells N, Linclau B, Sinnaeve D. J Org Chem 88 13908-13925 (2023)
  5. Reverse thiophosphorylase activity of a glycoside phosphorylase in the synthesis of an unnatural Manβ1,4GlcNAc library. Keenan T, Hatton NE, Porter J, Vendeville JB, Wheatley DE, Ghirardello M, Wahart AJC, Ahmadipour S, Walton J, Galan MC, Linclau B, Miller GJ, Fascione MA. Chem Sci 14 11638-11646 (2023)
  6. Synthetic Approaches to Break the Chemical Shift Degeneracy of Glycans. Dal Colle MCS, Fittolani G, Delbianco M. Chembiochem 23 e202200416 (2022)


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