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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
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) |
| Related URLs: | |
| 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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