TY - JOUR
T1 - Biotin and the nucleophilicity of 2-methoxy-2-imidazoline toward the sp2 carbonyl carbon
AU - Hegarty, A. F.
AU - Bruice, Thomas C.
AU - Benkovic, Stephen J.
N1 - Funding Information:
If the Brmsted rela- tion holds over this wide range (and there is precedent for this’), then Alog kIv -111must be of the order of 10 powers of 10. Similarly a rate constant of 6 x 104 1. mole-1 min.-I can be estimated4 for the uncatalysed reactioq of (111)with carbon dioxide at 10”. Although the concentration of the enol component of biotin is the immense reactivity difference between (111) and (IV) would appear to be consistent with a carboxylation route involving the enolized form. Any tendency to enolize biotin when bound to the enzymelo would of necessity greatly enhance its reactivity. This work was supported by grants from the Xational Institute of Arthritis and Metabolic Diseases and the Sational Science Foundation.
PY - 1969
Y1 - 1969
N2 - 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.
AB - 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.
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U2 - 10.1039/C29690001173
DO - 10.1039/C29690001173
M3 - Article
AN - SCOPUS:37049122811
SN - 0577-6171
SP - 1173
EP - 1174
JO - Analytical Proceedings
JF - Analytical Proceedings
ER -