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Metal ion-promoted cleavage of nucleoside diphosphosugars: a model for reactions of phosphodiester bonds in carbohydrates

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Abstract

Cleavage of five different nucleoside diphosphosugars has been studied in the presence of Cu2+ and Zn2+ complexes. The results show that metal ion catalysts promote the cleavage via intramolecular transesterification whenever a neighbouring HO group can adopt a cis-orientation with respect to the phosphate. The HO group attacks the phosphate and two monophosphate products are formed. If such a nucleophile is not available, Cu2+ complexes are able to promote a nucleophilic attack of an external nucleophile, e.g. a water molecule or metal ion coordinated HO ligand, on phosphate. With the Zn2+ complex, this was not observed.

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Authors and Affiliations

  1. Department of Chemistry, University of Turku, Vatselankatu 2, 20014, Turku, Finland

    Meisa Dano, Marjukka Elmeranta, Juho Jaakkola, Heidi Korhonen & Satu Mikkola

  2. Department of Chemistry, University of Durham, Science Labs, South Road, Durham, DH1 3LE, UK

    David R. W. Hodgson

Authors
  1. Meisa Dano
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  2. Marjukka Elmeranta
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  3. David R. W. Hodgson
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  4. Juho Jaakkola
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  5. Heidi Korhonen
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  6. Satu Mikkola
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Corresponding author

Correspondence to Satu Mikkola.

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Dano, M., Elmeranta, M., Hodgson, D.R.W. et al. Metal ion-promoted cleavage of nucleoside diphosphosugars: a model for reactions of phosphodiester bonds in carbohydrates. J Biol Inorg Chem 20, 1299–1306 (2015). https://doi.org/10.1007/s00775-015-1308-9

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  • DOI: https://doi.org/10.1007/s00775-015-1308-9

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