caa a22 4500 605507562 CHVBK 20210128100632.0 cr unu---uuuuu 210128e20151201xx s 000 0 eng 10.1007/s00775-015-1308-9 doi (NATIONALLICENCE)springer-10.1007/s00775-015-1308-9 Metal ion-promoted cleavage of nucleoside diphosphosugars: a model for reactions of phosphodiester bonds in carbohydrates [Elektronische Daten] [Meisa Dano, Marjukka Elmeranta, David Hodgson, Juho Jaakkola, Heidi Korhonen, Satu Mikkola] 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. Graphical Abstract: SBIC, 2015 Carbohydrates nationallicence Phosphodiesters nationallicence Cleavage nationallicence Mechanisms nationallicence Metal ion catalysts nationallicence Dano Meisa Department of Chemistry, University of Turku, Vatselankatu 2, 20014, Turku, Finland aut Elmeranta Marjukka Department of Chemistry, University of Turku, Vatselankatu 2, 20014, Turku, Finland aut Hodgson David Department of Chemistry, University of Durham, Science Labs, South Road, DH1 3LE, Durham, UK aut Jaakkola Juho Department of Chemistry, University of Turku, Vatselankatu 2, 20014, Turku, Finland aut Korhonen Heidi Department of Chemistry, University of Turku, Vatselankatu 2, 20014, Turku, Finland aut Mikkola Satu Department of Chemistry, University of Turku, Vatselankatu 2, 20014, Turku, Finland aut JBIC Journal of Biological Inorganic Chemistry Springer Berlin Heidelberg 20/8(2015-12-01), 1299-1306 0949-8257 20:8<1299 2015 20 775 https://doi.org/10.1007/s00775-015-1308-9 text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1007/s00775-015-1308-9 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Dano Meisa Department of Chemistry, University of Turku, Vatselankatu 2, 20014, Turku, Finland aut NATIONALLICENCE 700 1- Elmeranta Marjukka Department of Chemistry, University of Turku, Vatselankatu 2, 20014, Turku, Finland aut NATIONALLICENCE 700 1- Hodgson David Department of Chemistry, University of Durham, Science Labs, South Road, DH1 3LE, Durham, UK aut NATIONALLICENCE 700 1- Jaakkola Juho Department of Chemistry, University of Turku, Vatselankatu 2, 20014, Turku, Finland aut NATIONALLICENCE 700 1- Korhonen Heidi Department of Chemistry, University of Turku, Vatselankatu 2, 20014, Turku, Finland aut NATIONALLICENCE 700 1- Mikkola Satu Department of Chemistry, University of Turku, Vatselankatu 2, 20014, Turku, Finland aut NATIONALLICENCE 773 0- JBIC Journal of Biological Inorganic Chemistry Springer Berlin Heidelberg 20/8(2015-12-01), 1299-1306 0949-8257 20:8<1299 2015 20 775