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Published September 4, 2020 | Supplemental Material
Journal Article Open

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

Abstract

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.

Additional Information

© 2020 American Chemical Society. Received 19 June 2020. Published online 21 August 2020. Published in issue 4 September 2020. The authors thank David Kiemle (ESF Syracuse) for help with the acquisition of NMR spectra and Russell N. Burkhardt and Bennett W. Fox (Boyce Thompson Institute) for assistance with mass spectrometry. This work was partly supported by the National Institutes of Health (R35 GM131877 to F.C.S. and T32GM008500 to B.J.C.) and the Howard Hughes Medical Institute. The authors also thank the Packard Foundation (fellowship to H.M.N.) and Bristol Myers Squibb (Unrestricted Grant in Synthetic Organic Chemistry to H.M.N.) for generous support. The authors declare the following competing financial interest(s): F.C.S. is a founder of Ascribe Bioscience Inc. CCDC 2020283 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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Created:
August 19, 2023
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October 23, 2023