Oxidations of N-(3-indoleethyl) cyclic aliphatic amines by Horseradish peroxidase: The indole ring binds to the enzyme and mediates electron-transfer amine oxidation

KQ Ling, WS Li, LM Sayre

Index: Ling, Ke-Qing; Li, Wen-Shan; Sayre, Lawrence M. Journal of the American Chemical Society, 2008 , vol. 130, # 3 p. 933 - 944

Full Text: HTML

Citation Number: 12

Abstract

Although oxidations of aromatic amines by horseradish peroxidase (HRP) are well-known, typical aliphatic amines are not substrates of HRP. In this study, the reactions of N-benzyl and N-methyl cyclic amines with HRP were found to be slow, but reactions of N-(3- indoleethyl) cyclic amines were 2-3 orders of magnitude faster. Analyses of pH-rate profiles revealed a dominant contribution to reaction by the amine-free base forms, the only ...