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Review

Bond Formation at C8 in the Nucleoside and Nucleotide Purine Scaffold: An Informative Selection

by
Kjell Undheim
Department of Chemistry, University of Oslo, 0315 Oslo, Norway
Molecules 2024, 29(8), 1815; https://doi.org/10.3390/molecules29081815
Submission received: 6 March 2024 / Revised: 22 March 2024 / Accepted: 1 April 2024 / Published: 17 April 2024
(This article belongs to the Special Issue Collection of Scientific Papers by Outstanding Scientists in the Field of Bioorganic Chemistry)
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Abstract

This paper presents methods for the introduction and exchange of substituents in a nucleobase and its nucleosides and nucleotides with emphasis on the C8-position in the purine skeleton. The nucleobase is open for electrophilic and nucleophilic chemistry. The nucleophilic chemistry consists mainly of displacement reactions when the C8-substituent is a good leaving group such as a halogen atom. The heteroatom in amines, sulfides, or oxides is a good nucleophile. Halides are good reaction partners. Metal-promoted cross-coupling reactions are important for carbylations. Direct oxidative metalation reactions using sterically hindered metal amides offer chemo- and regio-selectivity besides functional tolerance and simplicity. The carbon site is highly nucleophilic after metalation and adds electrophiles resulting in chemical bond formation. Conditions for metal-assisted reactions are described for nucleobases and their glycosides.
Keywords: purine nucleobases; nucleosides and nucleotides; carbylations; oxidative metalations; cross-couplings; halogenations purine nucleobases; nucleosides and nucleotides; carbylations; oxidative metalations; cross-couplings; halogenations
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MDPI and ACS Style

Undheim, K. Bond Formation at C8 in the Nucleoside and Nucleotide Purine Scaffold: An Informative Selection. Molecules 2024, 29, 1815. https://doi.org/10.3390/molecules29081815

AMA Style

Undheim K. Bond Formation at C8 in the Nucleoside and Nucleotide Purine Scaffold: An Informative Selection. Molecules. 2024; 29(8):1815. https://doi.org/10.3390/molecules29081815

Chicago/Turabian Style

Undheim, Kjell. 2024. "Bond Formation at C8 in the Nucleoside and Nucleotide Purine Scaffold: An Informative Selection" Molecules 29, no. 8: 1815. https://doi.org/10.3390/molecules29081815

APA Style

Undheim, K. (2024). Bond Formation at C8 in the Nucleoside and Nucleotide Purine Scaffold: An Informative Selection. Molecules, 29(8), 1815. https://doi.org/10.3390/molecules29081815

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