Strong N-H⋅⋅⋅O Hydrogen Bonding in a Model Compound of the Catalytic Triad in Serine Proteases
Jacob Overgaard1, Birgit Schiøtt1, Finn K Larsen1
1Department of Chemistry, University of Aarhus, DK-8000 Aarhus (Denmark), Fax: (+45) 86196199.
Abstract:
Low-barrier hydrogen bond (LBHB) involvement in enzyme catalysis is examined by analysis of experimental nuclear and electron densities of a model compound for the catalytic triad in serine proteases (shown schematically), which is based on a cocrystal of betaine, imidazole, and picric acid. The three short, strong N-H⋅⋅⋅O hydrogen bonds in the structure have varying degrees of covalent bonding contributions suggesting a gradual transition to the LBHB situation.
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