Reactions catalyzed by oxidative enzymes, like laccases, in vitro often lead to the formation of a variety of different products. One example is the laccase/O2-catalyzed oxidation and oligomerization of the aniline dimer p-aminodiphenylamine (PADPA) in aqueous solution. For this reaction to be economically efficient for obtaining electrically conductive oligomeric products which resemble the emeraldine salt form of polyaniline (PANI-ES), the presence of vesicles formed from AOT, the sodium salt of bis(2-ethylhexyl)sulfosuccinate, is beneficial. This AOT vesicle-assisted enzymatic reaction was studied and optimized by using different in situ spectroscopic methods (UV/Vis/NIR, EPR, Raman) and a HPLC-MS analysis with partially deuterated PADPA and H218O. The vesicles play various roles in steering the reaction towards the desired PANI-ES-type products, favoring the para-NC-coupling of the reaction intermediates and suppressing unwanted hydrolytic side reactions. With this specific example, the role of dispersed soft interfaces as reaction regulators is discussed in the context of a number of other enzymatic and non-enzymatic reactions.

Steering an enzymatic reaction with vesicles

254th National Meeting (2017)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.