Identification of Uric Acid Gluconucleoside-Ascaroside Conjugates in Caenorhabditis elegans by Combining Synthesis and MicroED.

Autor: Curtis BJ; Boyce Thompson Institute and Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States., Kim LJ; Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States., Wrobel CJJ; Boyce Thompson Institute and Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States., Eagan JM; Ascribe Bioscience, Ithaca, New York 14853, United States., Smith RA; Boyce Thompson Institute and Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States., Burch JE; Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States., Le HH; Boyce Thompson Institute and Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States., Artyukhin AB; Chemistry Department, College of Environmental Science and Forestry, State University of New York, Syracuse, New York 13210, United States., Nelson HM; Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States., Schroeder FC; Boyce Thompson Institute and Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2020 Sep 04; Vol. 22 (17), pp. 6724-6728. Date of Electronic Publication: 2020 Aug 21.
DOI: 10.1021/acs.orglett.0c02038
Abstrakt: 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.
Databáze: MEDLINE