Wiley, Angewandte Chemie International Edition, 9(38), p. 1239-1242, 1999
DOI: 10.1002/(sici)1521-3773(19990503)38:9<1239::aid-anie1239>3.0.co;2-9
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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−HO hydrogen bonds in the structure have varying degrees of covalent bonding contributions suggesting a gradual transition to the LBHB situation.