Journal
TETRAHEDRON
Volume 59, Issue 11, Pages 2007-2014Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(03)00103-0
Keywords
siderophore; Marinobacter hydrocarbonoclasticus; synthesis; citrate; spermidine
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The total synthesis and the revised structural assignment of petrobactin, a siderophore isolated from the marine bacterium Marinobacter hydrocarbonoclasticus, is reported. The key step in the synthesis involved condensation of N'-(2,3-dibenzoyloxybenzoyl)N 4-benzylspermidine with 1,3-di-(p-nitrophenyl)-2-tert-butyI citrate. Proton NMR spectra of the synthesized product compared with those reported for the natural product revealed that the compound did not contain 2,3-dihydroxybenzoyl moieties as published; instead, the splitting pattern suggested 3,4-dihydroxybenzoyl fragments. The 3,4-dihydroxybenzoyl analogue was accessed via a similar route; the proton and carbon-13 NMR spectra of this compound were consistent with those reported for natural petrobactin. (C) 2003 Elsevier Science Ltd. All rights reserved.
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