The Role of α-Chymotrypsin Active Site in the Proton Dissociation of Aromatic Sulfonium-Salt Pendants Attached to the Methionine-192 Residue
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Hammett and <SUP>13</SUP>C NMR analyses of proton-dissociation processes for sulfonium-salt pendants on α-chymotrypsin which had been modified by 2-bromoacetophenone and its derivatives (as well as for their corresponding model sulfonium salts) show that a hydrophobic environment around the pendants destabilizes the sulfonium-salt form so as to substantially promote its proton-dissociation reaction. This produces a sulfonium ylide with a keto structure.
- Chemistry Letters
Chemistry Letters 1997(8), 719-720, 1997-08
The Chemical Society of Japan