2015
DOI: 10.4052/tigg.1423.1
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Recent Approaches to the Chemical Synthesis of Sugar Nucleoside Diphosphates

Abstract: Sugar nucleotides are important intermediates in carbohydrate metabolism and function as activated glycosyl donors for the biosynthesis of oligosaccharides. This review focuses on recent progress in the chemical synthesis of sugar nucleoside diphosphates.

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Cited by 6 publications
(12 citation statements)
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“…We highlight the emerging strategies that have been reviewed in recent years (e.g., cyclic dinucleotides). 5,32,34,236 We do not include the synthesis of nucleoside 5′-tetra-and 5′-pentaphosphates 31 or nucleoside cyclopyrophosphates 34 because readers can refer to summary reviews published in 2015.…”
Section: Miscellaneousmentioning
confidence: 99%
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“…We highlight the emerging strategies that have been reviewed in recent years (e.g., cyclic dinucleotides). 5,32,34,236 We do not include the synthesis of nucleoside 5′-tetra-and 5′-pentaphosphates 31 or nucleoside cyclopyrophosphates 34 because readers can refer to summary reviews published in 2015.…”
Section: Miscellaneousmentioning
confidence: 99%
“…34 When the NDP glycosylation approach is used, the yields are usually low, and in many cases, the stereochemistry at the anomeric center of the sugar in the final products cannot be controlled. 32,34 Regarding path B, a number of methods described for NDP or NTP synthesis have been adapted for the preparation of a variety of NDP-sugars, by substituting the phosphate or the pyrophosphate reagent with a sugar phosphate. These methods rely on intermediates, as already mentioned, such as phosphoromorpholidates, 260 phosphorimidazolates, 261 phosphoro-N-methylimidazolides, 262−264 zwitterionic pyrrolidinium ions, 265 5′-phosphoropiperidates, 242 phosphosulfonyl derivatives, 230 mixed P(III)−P(V) anhydrides, 266 and cycloSal phosphotriesters.…”
Section: Sugar Nucleotidesmentioning
confidence: 99%
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“…Methods for the chemical synthesis of nucleotides are based either on P III or P V chemistry (Hollenstein, 2012;Jessen, Ahmed, & Hofer, 2014;Johnson & Widlanski, 2004;Kore & Srinivasan, 2013;Roy, Depaix, Périgaud, & Peyrottes, 2016;Tanaka, 2015;Xu, 2015). Nucleoside phosphorimidazolides have been extensively used as intermediates for pyrophosphate bond formation in anhydrous organic solvents.…”
Section: Introductionmentioning
confidence: 99%