@article{adad795c5cb24a178dc84e78da71ccf9,
title = "Enzymatic synthesis of nucleobase-modified UDP-sugars: Scope and limitations",
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.",
keywords = "Enzymatic synthesis, Epimerase, Modified nucleobase, Pyrophosphatase, Sugar nucleotide",
author = "Wagstaff, {Ben A.} and Martin Rejzek and Thomas Pesnot and Tedaldi, {Lauren M.} and Lorenzo Caputi and O'Neill, {Ellis C.} and Stefano Benini and Wagner, {Gerd K.} and Field, {Robert A.}",
note = "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: {\textquoteleft}A structural genomics approach for the study of the virulence and pathogenesis of Erwinia amylovora {\textquoteright} and the Free University of Bolzano grant: Galactose and glucuronic acid metabolism in Erwinia spp. (GAMEs). Publisher Copyright: {\textcopyright} 2015 The Authors. Published by Elsevier Ltd.",
year = "2015",
month = mar,
day = "2",
doi = "10.1016/j.carres.2014.12.005",
language = "English",
volume = "404",
pages = "17--25",
journal = "Carbohydrate Research",
issn = "0008-6215",
publisher = "Elsevier",
}