A model for the biotin tautomer, 2-methoxy-2-imidazoline, possesses a nucleophilicity toward the sp2 carbonyl carbon 1010-fold greater than the previously considered 2-imidazolidone.
A. F. Hegarty, T. C. Bruice and S. J. Benkovic, J. Chem. Soc. D, 1969, 1173 DOI: 10.1039/C29690001173
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