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J. Biol. Chem., Vol. 281, Issue 8, 5209-5215, February 24, 2006

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A Major Cell Wall Lipopeptide of Mycobacterium avium subspecies paratuberculosis^*

Torsten M. Eckstein, Sukantha Chandrasekaran, Sebabrata Mahapatra, Michael R. McNeil, Delphi Chatterjee, Christopher D. Rithner, Philip W. Ryan^¶, John T. Belisle, and Julia M. Inamine¹

From the Department of Microbiology, Immunology, and Pathology, ^¶Macromolecular Research Facilities, and Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523

Mycobacterium avium subspecies paratuberculosis (MAP), the causative agent of Johne disease in cattle and other ruminants, is proposed to be at least one of the causes of Crohn disease in humans. MAP and Mycobacterium avium subspecies avium, a closely related opportunistic environmental bacterium, share 95% of their genes and exhibit homologies of more than 99% between these genes. The identification of molecules specific for MAP is essential for understanding its pathogenicity and for development of useful diagnostic tools. The application of gas chromatography, mass spectrometry, and nuclear magnetic resonance led to the structural identification of a major cell wall lipopeptide of MAP, termed Para-LP-01, defined as C20 fatty acyl-D-Phe-N-Me-L-Val-L-Ile-L-Phe-L-Ala methyl ester. Variations of this lipopeptide with different fatty acyl moieties (C16 fatty acyl through C17, C18, C19, C21 to C22) were also identified. Besides the specificity of this lipopeptide for MAP, the presence of an N-Me-L-valine represents the first reported N-methylated amino acid within an immunogenic lipopeptide of mycobacteria. Sera from animals with Johne disease, but not sera from uninfected cattle, reacted with this lipopeptide, indicating potential biological importance.

Received for publication, November 21, 2005 , and in revised form, December 5, 2005.

^* This work was supported by NIAID, National Institutes of Health Grant R01 AI-51283 (to J. M. I.). 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 Microbiology, Immunology, and Pathology, 1682 Campus Delivery, Colorado State University, Fort Collins, CO 80523-1682. Tel.: 970-491-7543; Fax: 970-491-1815; E-mail: jinamine{at}colostate.edu.

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