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The remarkable hydrophobic effect of a fatty acid side chain on the microbial growth promoting activity of a synthetic siderophore

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Abstract

The ability of synthetic derivatives of the siderophore tripeptide of N 5-hydroxy-N 5-acetyl-l-ornithine to promote the growth of various strains of mycobacteria and Gram negative bacteria was found to depend significantly on the hydrophobic nature of the derivative. Although the tripeptide of N 5-hydroxy-N 5-acetyl-l-ornithine is not normally utilized by mycobacteria, an N-terminal palmitoyl derivative mimicked natural mycobactin J in all studies.

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References

  • Benz G, Schröder T, Kurz J, Wünsche C, Karl W, Steffens G, Pfitzner J, Schmidt D. 1982 Konstitution der desferriform der albomycine ?1, ?2,., Angew Chem Suppl 1322–1335.

  • Lin Y-M, Miller MJ. 1999 Practical synthesis of hydroxamatederived siderophore components by an indirect oxidation method and syntheses of a DIG-siderophore conjugate and a biotinsiderophore conjugate. J Org Chem 64, 7451–7458.

    Google Scholar 

  • Martinez JS, Zhang GP, Hold PD, Jung H-T, Carrano C, Haygoodl MG, Butler A. 2000 Self-assembling amphiphilic siderophores from marine bacteria. Science 287, 1245–1247.

    Google Scholar 

  • Miller MJ, Malouin F. 1993 Microbial iron chelators as drug delivery agents: The rational design and synthesis of siderophore-drug conjugates. Accts Chem Res 26, 241–249.

    Google Scholar 

  • Miller MJ. 1989 Syntheses and therapeutic potential of hydroxamic acid based siderophores and analogs. Chem Rev 89, 1563–1579.

    Google Scholar 

  • Neilands JB. 1993 Siderophores. Arch Biochem Biophys 302, 1–3.

    Google Scholar 

  • Neilands JB. 1995 Siderophores: structure and function of microbial iron transport compounds. J Biol Chem 270, 26723–26726.

    Google Scholar 

  • Roosenberg JM II, Miller MJ. 2000 Total synthesis of the sideropohore danoxamine. J Org Chem 65, 4833–4838.

    Google Scholar 

  • Roosenberg JM, Lin Y-M, Lu Y, Miller MJ. 2000 Studies and syntheses of siderophore, microbial iron chelators, and analogs as potential drug delivery agents. Curr Med Chem 7, 159–197.

    Google Scholar 

  • Schumann G, Möllmann U, Heinemann I. Mutants of Mycobacterium species and their use for screening of antibiotic vectors. Patent application DE 1981 7021,9.(17.4.1998), Grünenthal GmbH.

  • Schumann G, Möllmann U. 2000 A screening system for xenosiderophores as potential drug delivery agents in Mycobacteria Antimicrob. Agents Chemother (in press).

  • Schwynn B, Neilands JB. 1987 Universal chemical assay for the detection and determination of siderophores. Anal Biochem 160, 47–56.

    Google Scholar 

  • Snapper SB, Melton RE, Mustafa, Kieser ST, Jacobs WR Jr. 1990 Isolation and characterization of efficient plasmid transformation mutants of Mycobacterium smegmatis. Mol Microbiol 4, 1911–1919.

    Google Scholar 

  • Vergne AF, Walz AJ, Miller MJ. 2000 Iron chelators from mycobacteria (1954–1999) and potential therapeutic applications. Nat. Prod Rep 17, 99–116.

    Google Scholar 

  • Wooldridge KG, Williams PH. 1993 Siderophores: structure and function of microbial iron transport compounds. FEMS Microbiol Rev 12, 325–348.

    Google Scholar 

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Lin, YM., Miller, M.J. & Möllmann, U. The remarkable hydrophobic effect of a fatty acid side chain on the microbial growth promoting activity of a synthetic siderophore. Biometals 14, 153–157 (2001). https://doi.org/10.1023/A:1016666414848

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  • DOI: https://doi.org/10.1023/A:1016666414848

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