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Metal–ion promoted cleavage of nucleoside diphosphosugars: A model for reactions of phosphodiester bonds in carbohydrates

Dano, Meisa; Elmeranta, Marjukka; Hodgson, David R.W.; Jaakkola, Juho; Korhonen, Heidi; Mikkola, Satu

Metal–ion promoted cleavage of nucleoside diphosphosugars: A model for reactions of phosphodiester bonds in carbohydrates Thumbnail


Authors

Meisa Dano

Marjukka Elmeranta

Juho Jaakkola

Heidi Korhonen

Satu Mikkola



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.

Citation

Dano, M., Elmeranta, M., Hodgson, D. R., Jaakkola, J., Korhonen, H., & Mikkola, S. (2015). Metal–ion promoted cleavage of nucleoside diphosphosugars: A model for reactions of phosphodiester bonds in carbohydrates. JBIC Journal of Biological Inorganic Chemistry, 20(8), 1299-1306. https://doi.org/10.1007/s00775-015-1308-9

Journal Article Type Article
Acceptance Date Oct 23, 2015
Online Publication Date Nov 7, 2015
Publication Date Dec 1, 2015
Deposit Date Oct 30, 2015
Publicly Available Date Nov 7, 2016
Journal JBIC Journal of Biological Inorganic Chemistry
Print ISSN 0949-8257
Electronic ISSN 1432-1327
Publisher Springer
Peer Reviewed Peer Reviewed
Volume 20
Issue 8
Pages 1299-1306
DOI https://doi.org/10.1007/s00775-015-1308-9
Keywords Carbohydrates, Phosphodiesters, Cleavage, Mechanisms, Metal ion catalysts.

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