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Intermediates 8 and 9 are only stable for a few minutes at pH 7 at 37°C However, they survive for hours at pH2 at room temperature (the equilibrium between the phenol and phenolate forms is shifted toward the phenol and elimination occurs only slowly). In the gal-catalyzed reactions, aliquots were withdrawn from the reaction medium and diluted with a solution of trifluoroacetic acid (to pH 2) before being injected into the HPLC apparatus with the mobile phase buffered at pH 2 (see the Supporting Information).
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Intermediates 8 and 9 are only stable for a few minutes at pH 7 at 37°C However, they survive for hours at pH2 at room temperature (the equilibrium between the phenol and phenolate forms is shifted toward the phenol and elimination occurs only slowly). In the gal-catalyzed reactions, aliquots were withdrawn from the reaction medium and diluted with a solution of trifluoroacetic acid (to pH 2) before being injected into the HPLC apparatus with the mobile phase buffered at pH 2 (see the Supporting Information).
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