Total synthesis of petrobactin and its homologues as potential growth stimuli for Marinobacter hydrocarbonoclasticus, an oil-degrading bacteria

    Authors

    R. A. Gardner; R. Kinkade; C. J. Wang;O. Phanstiel

    Comments

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    Abbreviated Journal Title

    J. Org. Chem.

    Keywords

    MARINE BACTERIUM; MOLECULAR REQUIREMENTS; IRON CHELATORS; SIDEROPHORE; BIOREMEDIATION; SCHIZOKINEN; INHIBITOR; Chemistry, Organic

    Abstract

    A modular synthesis was developed to access petrobactin, a catechol-containing siderophore isolated from Marinobacter hydrocarbonoclasticus. A range of petrobactin homologues with differing dihydroxybenzamide motifs and in one case an increased number of carbons in the polyamine backbone were also synthesized. As such, these systems represent new isomeric probes to study iron transport properties in M. hydrocarbonoclasticus. The synthesis of petrobactin and its homologues and the first biological study of how these agents influence the growth of Mycobacter hydrocarbonoclasticus are reported. New synthetic methods were developed to overcome issues (imide formation) encountered in earlier syntheses. Both the H-1 and C-13 NMR of petrobactin were consistent with the recently revised structure showing that petrobactin in fact contains a 3,4-dihydroxybenzene motif rather than a 2,3-dihydroxybenzene motif. The preliminary biological studies suggested that using the native petrobactin 1b for M. hydrocarbonoclasticus-specific growth stimulation may be a poor strategy for oil-spill cleanup.

    Journal Title

    Journal of Organic Chemistry

    Volume

    69

    Issue/Number

    10

    Publication Date

    1-1-2004

    Document Type

    Article

    Language

    English

    First Page

    3530

    Last Page

    3537

    WOS Identifier

    WOS:000221341100039

    ISSN

    0022-3263

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