- Identification of uric acid gluconucleoside-ascaroside conjugates in caenorhabditis elegans by combining synthesis and MicroED
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Few nucleoside-derived natural products have been identified from animals, despite the ubiquity of nucleosides in living organisms. Here, we use a combination of synthesis and the emerging electron microscopy technique microcrystal electron diffraction to determine the structures of several N3-(β-glucopyranosyl)uric acid derivatives in Caenorhabditis elegans. These noncanonical gluconucleosides further integrate an ascaroside moiety, for which we present a shortened synthetic route. The production of a phosphorylated gluconucleoside is influenced by evolutionarily conserved insulin signaling.
- Curtis, Brian J.,Kim, Lee Joon,Wrobel, Chester J.J.,Eagan, James M.,Smith, Rubin A.,Burch, Jessica E.,Le, Henry H.,Artyukhin, Alexander B.,Nelson, Hosea M.,Schroeder, Frank C.
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supporting information
p. 6724 - 6728
(2020/09/15)
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- AMMONOLYSIS OF PENTA-O-BENZOYL-α-D-GLUCOPYRANOSE IN AN APROTIC MEDIUM. CHARACTERIZATION OF THE PRODUCTS ISOLATED, AND CONFORMATIONAL ANALYSIS OF ELEVEN N-BENZOYL-D-GLUCOFURANOSYLAMINE DERIVATIVES
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The reaction of penta-O-benzoyl-α-D-glucopyranose with chloroform-1,4-dioxane-liquid ammonia gave 1,1-bis(benzamido)-6-O-benzoyl-1-deoxy-D-glucitol (29.0percent), three partially benzoylated derivatives of N-benzoyl-α-D-glucofuranosylamine (23.6percent), a small proportion of N-benzoyl-di-O-benzoyl-β-D-glucofuranosylamine (0.2percent), and four partially benzoylated derivatives of α-D-glucopyranose (9.9percent).The structures of the hitherto-unknown products, and their anomeric configurations, were established by chemical and spectroscopic methods.The conformations in solution of both anomers of N-benzoyl-D-glucofuranosylamine, their partially benzoylated derivatives isolated from the ammonolysis reaction, and the per-O-acetyl derivatives of the various compounds were analyzed by (1)H-n.m.r.spectroscopy.
- Salinas, Amelia E.,Sproviero, Jorge F.,Deulofeu, Venancio
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