Open AccessIdentification of Uric Acid Gluconucleoside–Ascaroside Conjugates in Caenorhabditis elegans by Combining Synthesis and MicroED
Author(s) -
Brian J Curtis,
Lee Joon Kim,
Chester J J Wrobel,
James M. Eagan,
Rubin A. Smith,
Jessica E. Burch,
Henry Le,
Alexander B. Artyukhin,
Hosea M. Nelson,
Frank C. Schroeder
Publication year - 2020
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c02038
Subject(s) - caenorhabditis elegans , chemistry , nucleoside , moiety , uric acid , biochemistry , combinatorial chemistry , stereochemistry , gene
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 N 3 -(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.