Abstract
Acetylcholinesterase (AChE) is the crucial enzyme in the central nervous
system. It is the target of various organophosphorus nerve agents and
pesticides, and the inhibition of AChE is a therapeutic strategy for the
treatment of various neurological-related diseases. The Glu202 is a key
residue adjacent to the catalytic His447 and plays important role in
catalysis. Although the Glu202 has long been considered as negatively
charged in many studies, more and more evidences support a protonated
Glu202. However, Glu202 is freely accessible by solvent, and thus it
seems more reasonable for Glu202 to majorly take the deprotonated state.
In the present work, we carried out a series of molecular dynamics
simulations with the Glu202 adopting different protonation states. Our
results show that the protonated Glu202 is important in maintaining the
key hydrogen bond network that supports the catalytic triad, whereas the
deprotonated Glu202 results in the collapse of the key hydrogen bond
network which consequently destabilizes the catalytic His447. We also
notice that different protonation states of Glu202 merely alters the
binding mode of ACh. However, since the catalytic His447 is disrupted if
Glu202 is deprotonated, His447 can not facilitate the nucleophilic
attack performed by Ser203. Therefore, the catalytic efficiency of ACh
hydrolysis should be remarkably decreased if Glu202 is deprotonated. Our
findings suggest that, when designing and developing highly active AChE
inhibitors or proposing mechanistic hypotheses for AChE-catalyzed
reactions, the protonated state of Glu202 should be considered.