AI Article Synopsis
- Several proteases, particularly pepsin, have been found to effectively catalyze asymmetric aldol reactions, demonstrating their versatility beyond traditional roles.
- Pepsin showed good efficiency in a specific reaction involving acetone and 4-nitrobenzaldehyde, yielding high amounts of product with decent enantioselectivity while maintaining its structure under neutral pH conditions.
- The stability of pepsin over multiple reaction cycles suggests its potential in sustainable organic synthesis methods, broadening the scope of protease applications in chemistry.
Article Abstract
Several proteases, especially pepsin, were observed to directly catalyze asymmetric aldol reactions. Pepsin, which displays well-documented proteolytic activity under acidic conditions, exhibited distinct catalytic activity in a crossed aldol reaction between acetone and 4-nitrobenzaldehyde with high yield and moderate enantioselectivity. Fluorescence experiments indicated that under neutral pH conditions, pepsin maintains its native conformation and that the natural structure plays an important role in biocatalytic promiscuity. Moreover, no significant loss of enantioselectivity was found even after four cycles of catalyst recycling, showing the high stability of pepsin under the selected aqueous reaction conditions. This case of biocatalytic promiscuity not only expands the application of proteases to new chemical transformations, but also could be developed into a potentially valuable method for green organic synthesis.
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| http://dx.doi.org/10.1016/j.jbiotec.2010.10.004 | DOI Listing |
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