Biosynthesis of the 3,4-dihydroxybenzoate moieties of petrobactin by Bacillus anthracis

Andrew T. Koppisch, Kinya Hotta, David T. Fox, Christy E. Ruggiero, Chu Young Kim, Timothy Sanchez, Srinivas Iyer, Cindy C. Browder, Pat J. Unkefer, Clifford J. Unkefer

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19 Scopus citations

Abstract

(Chemical Equation Presented) The biosynthesis of the 3,4-dihydroxybenzoate moieties of the siderophore petrobactin, produced by B. anthracis str. Sterne, was probed by isotopic feeding experiments in iron-deficient media with a mixture of unlabeled and D-[13C6]glucose at a ratio of 5:1 (w/w). After isolation of the labeled siderophore, analysis of the isotopomers was conducted via one-dimensional 1H and 13C NMR spectroscopy, as well as 13C-13C DQFCOSY spectroscopy. Isotopic enrichment and 13C-13C coupling constants in the aromatic ring of the isolated siderophore suggested the predominant route for the construction of the carbon backbone of 3,4-DHB (1) involved phosphoenol pyruvate and erythrose-4-phosphate as ultimate precursors. This observation is consistent with that expected if the shikimate pathway is involved in the biosynthesis of these moieties. Enrichment attributable to phosphoenol pyruvate precursors was observed at C1 and C6 of the aromatic ring, as well as into the carboxylate group, while scrambling of the label into C2 was not. This pattern suggests 1 was biosynthesized from early intermediates of the shikimate pathway and not through later shikimate intermediates or aromatic amino acid precursors.

Original languageEnglish (US)
Pages (from-to)5759-5765
Number of pages7
JournalJournal of Organic Chemistry
Volume73
Issue number15
DOIs
StatePublished - Aug 1 2008

ASJC Scopus subject areas

  • Organic Chemistry

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    Koppisch, A. T., Hotta, K., Fox, D. T., Ruggiero, C. E., Kim, C. Y., Sanchez, T., Iyer, S., Browder, C. C., Unkefer, P. J., & Unkefer, C. J. (2008). Biosynthesis of the 3,4-dihydroxybenzoate moieties of petrobactin by Bacillus anthracis. Journal of Organic Chemistry, 73(15), 5759-5765. https://doi.org/10.1021/jo800427f