Enzymatic synthesis of nucleobase-modified UDP-sugars:Scope and limitations

Wagstaff, Ben A., Rejzek, Martin, Pesnot, Thomas, Tedaldi, Lauren M., Caputi, Lorenzo, O'Neill, Ellis C., Benini, Stefano, Wagner, Gerd K. and Field, Robert A. ORCID: https://orcid.org/0000-0001-8574-0275 (2015) Enzymatic synthesis of nucleobase-modified UDP-sugars:Scope and limitations. Carbohydrate Research, 404. pp. 17-25. ISSN 0008-6215

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Abstract

Glucose-1-phosphate uridylyltransferase in conjunction with UDP-glucose pyrophosphorylase was found to catalyse the conversion of a range of 5-substituted UTP derivatives into the corresponding UDP-galactose derivatives in poor yield. Notably the 5-iodo derivative was not converted to UDP-sugar. In contrast, UDP-glucose pyrophosphorylase in conjunction with inorganic pyrophosphatase was particularly effective at converting 5-substituted UTP derivatives, including the iodo compound, into a range of gluco-configured 5-substituted UDP-sugar derivatives in good yields. Attempts to effect 4″-epimerization of these 5-substituted UDP-glucose with UDP-glucose 4″-epimerase from yeast were unsuccessful, while use of the corresponding enzyme from Erwinia amylovora resulted in efficient epimerization of only 5-iodo-UDP-Glc, but not the corresponding 5-aryl derivatives, to give 5-iodo-UDP-Gal. Given the established potential for Pd-mediated cross-coupling of 5-iodo-UDP-sugars, this provides convenient access to the galacto-configured 5-substituted-UDP-sugars from gluco-configured substrates and 5-iodo-UTP.

Item Type: Article
Additional Information: Funding Information: This work was supported by the UK BBSRC Institute Strategic Programme Grant on Understanding and Exploiting Metabolism (MET) [ BB/J004561/1 ] and the John Innes Foundation, with additional support by the EPSRC (First Grant EP/D059186/1 , to G.K.W.) and the MRC (Grant No. 0901746 , to G.K.W.). We thank Dr. M. Malnoy for providing E. amylovora genomic DNA. Plasmid pETM-30 was obtained from the European Molecular Biology Laboratory under a signed Material Transfer Agreement. Part of this work (cloning, overexpression and purification of Ea GalE) was supported by the Autonomous Province of Bolzano grant: ‘A structural genomics approach for the study of the virulence and pathogenesis of Erwinia amylovora ’ and the Free University of Bolzano grant: Galactose and glucuronic acid metabolism in Erwinia spp. (GAMEs). Publisher Copyright: © 2015 The Authors. Published by Elsevier Ltd.
Uncontrolled Keywords: enzymatic synthesis,epimerase,modified nucleobase,pyrophosphatase,sugar nucleotide,analytical chemistry,biochemistry,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1600/1602
Faculty \ School: Faculty of Science > School of Chemistry, Pharmacy and Pharmacology
Faculty of Science > School of Pharmacy (former - to 2024)
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Depositing User: LivePure Connector
Date Deposited: 04 Sep 2024 13:35
Last Modified: 25 Sep 2024 18:06
URI: https://ueaeprints.uea.ac.uk/id/eprint/96538
DOI: 10.1016/j.carres.2014.12.005

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