Meisa Dano
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
Authors
Marjukka Elmeranta
Professor David Hodgson d.r.w.hodgson@durham.ac.uk
Professor
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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Copyright Statement
The final publication is available at Springer via http://dx.doi.org/10.1007/s00775-015-1308-9.
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