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Model aldol bioconjugation between (a) phenylalanine aldehyde 4 and ketones (5-7) catalyzed by proline. (b) Comparison of uncatalyzed and proline-catalyzed (100 mM) reaction rates in DMSO at 37°C between 4 (1 equiv., 7mM) and hydroxyacetone 6 (12 equiv., 84 mM). (c) Comparison of reaction in 100% DMSO versus 1:1 sodium phosphate buffer (pH 7.4): DMSO. (d) Proposed role of water in increasing reaction kinetics.
