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. Author manuscript; available in PMC: 2018 Feb 9.
Published in final edited form as: J Med Chem. 2016 Dec 20;60(3):839–885. doi: 10.1021/acs.jmedchem.6b00788

Table 4.

Rate Constants for Reaction of α-Methylene-γ-lactones with Cysteine

Compound Rate Constant (M−1s−1)a
195 1.7
Elephantopin (192) 43
Iodoacetamide 25
Eupatundin (193) ~42b
Vernolepin (194) ~200b
N-ethylmaleimide 3750
a

Reported second order rate constants with cysteine (2 equivalents) in aqueous buffer (pH = 7.4)

b

The kinetics for the addition of cysteine to 193 and 194 were nonlinear, so the rate constants were calculated from initial rates.