Dess–Martin periodinane-mediated oxidation of the primary alcohol of cytidine into a carboxylic acid
Serre, Alexandra R.E. Rivault, Adele Eriksson, L.A.,
Serre, Alexandra R.E.
Rivault, Adele
Eriksson, L.A.,
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2024-05-21
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© 2024 The Authors. Published by the Royal Society of Chemistry. Open access article. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
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2024-04-16
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Abstract
Herein the first example of conversion of alcohols into carboxylic acids by use of the Dess-Martin Periodinane (DMP), which is otherwise routinely employed for the conversion to aldehydes, is reported. This methodology will have significant potential utility in the synthesis of cytidine analogues and other related biologically important molecules.
Cytidine is a nucleoside that plays many roles in biological systems. It is a component of DNA, and also commonly features in enzyme substrates, such as cytidine monophosphate-sialic acid. Due to its essential biological importance, multiple analogues have been developed. In our endeavors to synthesise analogues of cytidine as potential glycosyltransferase inhibitors, we required introduction of an aldehyde at the 5′-alcohol of ribose as a synthetic intermediate. Based on its wide use as a mild and selective reagent to oxidise such alcohols to aldehydes, we selected DMP as a suitable reagent for this purpose. To our surprise, we found that DMP further oxidised the primary alcohol of cytidine to the carboxylic acid, rather than the expected aldehyde.
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Serre ARE, Jha V, Rivault A, et al (2024) Dess–Martin periodinane-mediated oxidation of the primary alcohol of cytidine into a carboxylic acid. Organic and Biomolecular Chemistry. 22: 3848-3853.
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