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Structure of mycobactin J

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Abstract

Mycobactin J-1, an iron chelate fromMycobacterium paratuberculosis, was characterized by mass spectrum and by1H nuclear magnetic resonance (NMR) and13C NMR spectra of the parent molecule and of cobactin J-1. The core structure of mycobactin J-1 contained the phenyloxazoline ring system common to the mycobactins. The benzene ring was disubstituted. The two hydroxamate functions were furnished by 1 linear 6-N-hydroxylysine residue and 1 cyclic 6-N-hydroxylysine residue as in other members of this class of compounds. The acyl function at the mycobactic acid hydroxamate center wasn-cis-hexadec-2-enoyl. The hydroxyacid of the cobactin portion of mycobactin J-1 was 2,4-dimethyl-3-hydroxypentanoic acid. This latter residue differs from those of other known mycobactins by the presence of the isopropyl group.

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Authors and Affiliations

  1. National Animal Disease Center, Agricultural Research Service, Science and Education, U.S. Department of Agriculture, P.O. Box 70, 50010, Ames, Iowa, USA

    Willard G. McCullough & Richard S. Merkal

Authors
  1. Willard G. McCullough
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  2. Richard S. Merkal
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McCullough, W.G., Merkal, R.S. Structure of mycobactin J. Current Microbiology 7, 337–341 (1982). https://doi.org/10.1007/BF01572600

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