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

Nucleosides and nucleotides are a group of small molecule effectors and substrates which include sugar nucleotides, purine and pyrimidine-based nucleotide phosphates, and diverse nucleotide antibiotics. We previously reported that hydrogenation of the nucleotide antibiotic tunicamycin leads to produ...

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Bibliographic Details
Published in:Carbohydrate research 2020-02, Vol.488, p.107893-107893, Article 107893
Main Authors: Price, Neil P.J., Jackson, Michael A., Vermillion, Karl E., Blackburn, Judith A., Hartman, Trina M.
Format: Article
Language:English
Subjects:
5,6-Dihydropyrimidines
Catalytic hydrogenation
Pyrimidines
Sugar nucleotides
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Summary:Nucleosides and nucleotides are a group of small molecule effectors and substrates which include sugar nucleotides, purine and pyrimidine-based nucleotide phosphates, and diverse nucleotide antibiotics. We previously reported that hydrogenation of the nucleotide antibiotic tunicamycin leads to products with reduced toxicity on eukaryotic cells. We now report the hydrogenation of diverse sugar nucleosides, nucleotide phosphates, and pyrimidine nucleotides. UDP-sugars and other uridyl and thymidinyl nucleosides are quantitatively reduced to the corresponding 5,6-dihydro-nucleosides. Cytidyl pyrimidines are reduced, but the major products are the corresponding 5,6-dihydrouridyl nucleosides resulting from a deamination of the cytosine ring. [Display omitted] •Quantitative catalytic hydrogenation of pyrimidines.•Nucleosides, nucleotide phosphates, and sugar nucleotides.•Ring opening of 5,6-DH-uridyl and 5,6-DH-thymidyl bases.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2019.107893