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ARS Home » Midwest Area » Peoria, Illinois » National Center for Agricultural Utilization Research » Renewable Product Technology Research » Research » Publications at this Location » Publication #367043

Research Project: Technologies for Producing Renewable Bioproducts

Location: Renewable Product Technology Research

Title: Rhodium-catalyzed reductive modification of pyrimidine nucleosides, nucleotide phosphates, and sugar nucleotides.

Author
item Price, Neil
item Jackson, Michael - Mike
item Vermillion, Karl
item Blackburn, Judith
item Hartman, Trina

Submitted to: Carbohydrate Research
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 8/20/2019
Publication Date: 12/30/2019
Citation: Price, N.P., Jackson, M.A., Vermillion, K., Blackburn, J.A., Hartman, T.M. 2019. Rhodium-catalyzed reductive modification of pyrimidine nucleosides, nucleotide phosphates, and sugar nucleotides. Carbohydrate Research. 488(2020): 107893. https://doi.org/10.1016/j.carres.2019.107893.
DOI: https://doi.org/10.1016/j.carres.2019.107893

Interpretive Summary: Nucleoside antibiotics are a well-known group that include several antibacterial, antiviral, and antifungal agents. We previously devised a method called hydrogenation that was used to chemically modify one of these antibiotics to reduce toxicity while still maintaining antimicrobial activity. The goal of this work was to optimize this hydrogenation process with several uridine- and thymidine-type nucleosides so this technology could be applied to other nucleoside antibiotics. These results provide valuable information for the development of new and improved antibiotics for use in agriculture and medicine.

Technical Abstract: This study reports a catalytic hydrogenation of biologically-relevant sugar nucleotides, nucleotide phosphates, and pyrimidine nucleosides. The uridyl and thymidinyl compounds are quantitatively reduced to the corresponding 5, 6-dihydro-nucleosides. The cytidyl pyrimidines are also reduced, but unexpectedly the major products were the corresponding 5, 6-dihydrouridyl nucleosides resulting from a deamination of the cytosine ring. A base-catalyzed ring opening of the 5, 6-dihydropyrimidine bases is also reported, and antimicrobial properties have been assessed.