Abstract
A new type of fluorogenic alkyldiacyl glycerols was synthesized and used as fluorogenic substrates for the analysis of lipase activities and stereoselectivities. These compounds contain pyrene or perylene as a fluorophore and the trinitrophenyl-amino- (TNP) residue as a quencher. Both substituents are covalently bound to the ω-ends of the sn-2 and sn-1(3) acyl chains, respectively. Upon glycerolipid hydrolysis, the residues are separated from each other thus allowing determination of lipase activity from the continuous increase in fluorescence intensity which is caused by dequenching. Mixtures of enantiomeric fluorogenic alkyldiacyl glycerols, selectively labeled with pyrene or perylene as fluorophores, can be used for a dual-wavelength ‘stereoassay’ of lipases. Since absorption and emission maxima of both labels are clearly separated, hydrolysis of the respective enantiomeric substrates can be distinguished simultaneously, and the difference in their rates of hydrolysis can be taken as a parameter for the stereopreference of a lipase.
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