Abstract
Azobenzene-3,3'-dicarboxylic acid exists in photoisomerizable (E) and (Z)-forms. Deprotonation of the carboxylic acid groups from the (E)-form occurs simultaneously, whereas in the (Z)-form it occurs in a stepwise fashion. The mono anionic form of the (Z)-isomer acts as a glycosidase mimic that proceeds through a general acid-general base catalytic mechanism. This is the first example of a photoresponsive glycosidase mimic.
Highlights
Biological functions can be regulated by pH, ions or signalling molecules
The mono anionic form of the (Z)-isomer acts as a glycosidase mimic that proceeds through a general acid–general base catalytic mechanism
It was thought that (E)–(Z) isomerization of azobenzene-3,30dicarboxylic acid might lead to the modulation of pKa values of the two acid groups
Summary
Biological functions can be regulated by pH, ions or signalling molecules. Certain biological events can be regulated by light stimuli. The mono anionic form of the (Z)-isomer acts as a glycosidase mimic that proceeds through a general acid–general base catalytic mechanism. A per-O-methylated cyclodextrin based diacid has been used by Bols and co-workers to catalyze the glycosidic bond cleavage with appreciable rate enhancement.18e to date there has not been any report on the regulation of the glycosidase activity of enzyme mimics with light.
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