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. Author manuscript; available in PMC: 2018 Aug 30.
Published in final edited form as: J Am Chem Soc. 2017 Aug 16;139(34):11670–11673. doi: 10.1021/jacs.7b05125

Figure 1.

Figure 1

5HTP 2 exhibit significantly higher reactivity toward aryl diazonium ions relative to Tyr 1. (A) Azo-coupling reaction of aryldiazoniums with Tyr and 5HTP. (B) Structures of aryl-diazonium ions used. (C) Observed rate of azo-coupling reaction of 4NDz 3 with 5HTP and Tyr at indicated concentrations in 100 mM phosphate buffer (pH 7, room temperature). (D) Measurement of the rate of the azo-coupling reaction between 4CDz and 5HTP under pseudo-first-order conditions. (E) Second-order rate constants of the azo-coupling reactions between the indicated partners (M−1 s −1). Each rate represents an average of three independent experiments, and error represents standard deviation.