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J. Biol. Chem., Vol. 282, Issue 31, 22364-22369, August 3, 2007

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In Vitro Synthesis of Oleoylglycine by Cytochrome c Points to a Novel Pathway for the Production of Lipid Signaling Molecules^*

From the Department of Anatomy, Physiology, and Genetics, F. Edward Hebert School of Medicine, Uniformed Services University of the Health Sciences, Bethesda, Maryland 20814

Long chain fatty acyl glycines represent a new class of signaling molecules whose biosynthetic pathway is unknown. Here we report that cytochrome c catalyzes the formation of oleoylglycine from oleoyl-CoA and glycine, in the presence of hydrogen peroxide. The identity of oleoylglycine product was confirmed by isotope labeling and fragmentation mass spectrometry. Synthesis of oleoylglycine by cytochrome c was dependent upon substrate concentration and time. Other heme-containing proteins, myoglobin and hemoglobin, did not catalyze oleoylglycine synthesis. The functional properties of the reaction closely resemble those observed for the ability of cytochrome c to mediate the synthesis of oleamide from oleoyl-CoA and ammonia, in the presence of hydrogen peroxide (Driscoll, W. J., Chaturvedi., S., and Mueller, G. P. (2007) J. Biol. Chem. 282). The ability of cytochrome c to catalyze the formation of oleoylglycine experimentally indicates the potential importance of cytochrome c as a novel mechanism for the generation of long chain fatty acyl glycine messengers in vivo.

Received for publication, March 1, 2007 , and in revised form, May 29, 2007.

^* This work was supported by NINDS, National Institutes of Health Grant R01 NS38050-03 (to G. P. M.). The costs of publication of this article were defrayed in part by the payment of page charges. This article must therefore be hereby marked "advertisement" in accordance with 18 U.S.C. Section 1734 solely to indicate this fact.

¹ To whom correspondence should be addressed: Dept. of Anatomy, Physiology, and Genetics, USUHS, 4301 Jones Bridge Rd., Bethesda, MD 20814-4799. Tel.: 301-295-3507; Fax: 301-295-3566; E-mail: gmueller{at}usuhs.mil.

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