Metal ion‑promoted cleavage of nucleoside diphosphosugars: a model for reactions of phosphodiester bonds in carbohydrates
: Meisa Dano, Marjukka Elmeranta, David R.W.Hodgson, Juho Jaakkola, Heidi Korhonen, Satu Mikkola
Publisher: Springer
: 2015
: Journal of Biological Inorganic Chemistry
: JBIC
: 20
: 8
: 1299
: 1306
: 8
: 0949-8257
DOI: https://doi.org/10.1007/s00775-015-1308-9
Cleavage of five different nucleoside diphos-
phosugars has been studied in the presence of Cu 2 + and
Zn 2 + complexes. The results show that metal ion catalysts
promote the cleavage via intramolecular transesterifica -
tion 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, Cu 2 + com-
plexes are able to promote a nucleophilic attack of an exter-
nal nucleophile, e.g. a water molecule or metal ion coor-
dinated HO ligand, on phosphate. With the Zn 2 + complex,
this was not observed.