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J. Biochem, 2003, Vol. 133, No. 5 679-685
© 2003 Japanese Biochemical Society

BIOCHEMISTRY

The Formation of the 7-Carboxyheptyl Radical from 13-Hydroperoxy-9,11-Octadecadienoic Acid Catalyzed by Hemoglobin and Myoglobin under Anaerobic Conditions

Hideo Iwahashi+,1, Kazumasa Kumamoto2 and Tomihiro Hirai3

1 Department of Chemistry, Wakayama Medical University, 811-1 Kimiidera, Wakayama 641-8509; 2 Institute of Health and Sports Science, Kinki University, Higashiosaka, Osaka 577-8502; and 3 Faculty of Health and Sport Sciences, Osaka University, 1-17 Machikaneyama, Toyonaka, Osaka 560-0043

Methemoglobin (MetHb), oxyhemoglobin (oxyHb), metmyoglobin (metMb), and oxymyoglobin (oxyMb) catalyze formation of the 7-carboxyheptyl and pentyl radicals from 13-hydroperoxy-9,11-octadecadienoic acid. The relative HPLC-ESR peak height of the pentyl radical to the 7-carboxyheptyl radical was found to depend on the oxygen concentration in the reaction mixture. Under aerobic conditions, the 7-carboxyheptyl radical was predominant for the reaction mixture with ferrous ions (or cytochrome c, metHb, or metMb). On the other hand, under anaerobic conditions, the pentyl radical was predominant for the reaction mixture with ferrous ions (or cytochrome c), but the 7-carboxyheptyl radical was still predominant for the reaction mixture with metHb (or metMb), suggesting that metHb (or metMb) catalyzes the reaction through a mechanism different from that in the case of ferrous ions (or cytochrome c). In order to explain the above results, a mechanism, in which molecular oxygen is not involved, is proposed for the formation of the 7-carboxyheptyl radical in the reaction mixture of 13-HPODE with metHb (or metMb) under anaerobic conditions.

+ To whom correspondence should be addressed. Tel: +81-73-441-0772, Fax: +81-73-441-0772, E-mail: chem1{at}wakayama-med.ac.jp


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