Catalysis of the photo-Fries reaction: antibody-mediated stabilization of high energy states

TJ Dickerson, MR Tremblay, TZ Hoffman…

Index: Dickerson, Tobin J.; Tremblay, Martin R.; Hoffman, Timothy Z.; Ruiz, Diana I.; Janda, Kim D. Journal of the American Chemical Society, 2003 , vol. 125, # 50 p. 15395 - 15401

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Citation Number: 12

Abstract

A conformationally constrained hapten is presented that is capable of catalyzing the first antibody-mediated photo-Fries rearrangement. In this reaction, absorption of light energy by a diphenyl ether substrate results in homolytic CO bond cleavage followed by recombination to yield biphenyl-derived products. The most proficient antibody studied converts 4- phenoxyaniline 15 into 2-hydroxy-5-aminobiphenyl 16 under high-intensity irradiation at a ...