Journal
CARBOHYDRATE RESEARCH
Volume 404, Issue -, Pages 17-25Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2014.12.005
Keywords
Sugar nucleotide; Modified nucleobase; Enzymatic synthesis; Pyrophosphatase; Epimerase
Funding
- UK BBSRC Institute Strategic Programme Grant on Understanding and Exploiting Metabolism (MET) [BB/J004561/1]
- John Innes Foundation
- EPSRC [EP/D059186/1]
- MRC [0901746]
- Autonomous Province of Bolzano grant: 'A structural genomics approach for the study of the virulence and pathogenesis of Erwinia amylovora'
- Free University of Bolzano grant: Galactose and glucuronic acid metabolism in Erwinia spp. (GAMEs)
- Biotechnology and Biological Sciences Research Council [BBS/E/J/000C0618] Funding Source: researchfish
- Engineering and Physical Sciences Research Council [EP/D059186/1] Funding Source: researchfish
- BBSRC [BBS/E/J/000C0618] Funding Source: UKRI
- EPSRC [EP/D059186/1] Funding Source: UKRI
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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 400-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. (C) 2015 The Authors. Published by Elsevier Ltd.
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