Transesterification of phosphodiester by a zinc-containing cyclen derivative

Identification of the active species

authored by
Markus Kalesse, Andrea Loos
Abstract

The active site analogue 2 of alkaline phosphatase was synthesized and its hydrolytic activity was tested. Efficient hydrolysis was observed at pH > 8 at various concentrations of the hydrolytic species. The cyclic phosphate 3 derived from transesterification could be identified by 31P-NMR spectroscopy. A comparison of the hydrolysis results with the species distribution curve revealed the ZnL-OH species as the active complex. The complex stability constant (log KZnL) of ligand 7 was determined to be 13.7 (± 0.5). K′ for the hydrolysis of the p-nitrophenyl phosphate ester of propylene glycol (1) with 2 (0.02 M, pH = 8.35) is 1.5 × 10-3 s-1 at 50°C.

Organisation(s)
Institute of Organic Chemistry
Type
Article
Journal
Liebigs Annales
Pages
935-939
No. of pages
5
ISSN
0947-3440
Publication date
06.1996
Publication status
Published
Peer reviewed
Yes
ASJC Scopus subject areas
General Chemistry
Electronic version(s)
https://doi.org/10.1002/jlac.199619960611 (Access: Unknown)