title: A major cell wall lipopeptide of Mycobacterium avium subspecies paratuberculosis.
abstract: 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.
authors.affiliation: Department of Microbiology, Immunology, and Pathology, Colorado State University, Fort Collins, Colorado 80523-1682, USA.
authors.forename: Torsten M
authors.initials: TM
authors.lastname: Eckstein
authors.forename: Sukantha
authors.initials: S
authors.lastname: Chandrasekaran
authors.forename: Sebabrata
authors.initials: S
authors.lastname: Mahapatra
authors.forename: Michael R
authors.initials: MR
authors.lastname: McNeil
authors.forename: Delphi
authors.initials: D
authors.lastname: Chatterjee
authors.forename: Christopher D
authors.initials: CD
authors.lastname: Rithner
authors.forename: Philip W
authors.initials: PW
authors.lastname: Ryan
authors.forename: John T
authors.initials: JT
authors.lastname: Belisle
authors.forename: Julia M
authors.initials: JM
authors.lastname: Inamine
mesh_terms: D000818:Animals; D002417:Cattle; D002418:Cattle Diseases / Q000382:microbiology; D002473:Cell Wall / Q000378:metabolism*; D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D004797:Enzyme-Linked Immunosorbent Assay; D005227:Fatty Acids / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D006868:Hydrolysis; D008055:Lipids / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009162:Mycobacterium avium / Q000378:metabolism*; D016927:Mycobacterium avium subsp. paratuberculosis / Q000378:metabolism; D010283:Paratuberculosis / Q000382:microbiology*; D010455:Peptides / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013379:Substrate Specificity
chemical_list: D005227:Fatty Acids; D008055:Lipids; D010455:Peptides