156880-89-6Relevant articles and documents
Models for Enzyme-catalysed Phosphate Transfer: Comparisons of Reactivity towards a Neighbouring Hydroxy Group for Phosphodiester Anions and Acids. General Base Catalysis of the Cyclisation of a Hydroxyalkyl Phosphate Triester
Chandler, Anthony J.,Hollfelder, Florian,Kirby, Anthony J.,O'Carroll, Fiona,Stroemberg, Roger
, p. 327 - 334 (2007/10/02)
Methylation of phenyl 1,2-isopropylidene-β-D-xylofuranose 3'-phosphate increases the rate of intramolecular cyclisation by a factor of over 1E5.This confirms previous estimates of the effect of protonation on the reactivity of phosphate diesters towards a neighbouring hydroxy group, which depnd on the correct assignment of kinetically equivalent mechanisms, and makes available reliable data on the magnitude of the effect for reactions catalysed by a range of general acids and bases.General base catalysis is characterised for the intramolecular cyclisation of one diastereoisomer (7b) of methyl phenyl 1,2-isopropylidene-β-D-xylofuranose 3'-phosphate triester: the Broensted β is 0.65 and catalysis is enhanced by the proximity of the positive centres of suitable diamine monocations.