The remarkable hydrophobic effect of a fatty acid side chain on the microbial growth promoting activity of a synthetic siderophore.
The ability of synthetic derivatives of the siderophore tripeptide of N5-hydroxy-N5-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 N5-hydroxy-N5-acetyl-L-ornithine is not normally utilized by mycobacteria, an N-terminal palmitoyl derivative mimicked natural mycobactin J in all studies.
Lin
Y M
YM
Department of Chemistry and Biochemistry, University of Notre Dame, IN 46556, USA.
Miller
M J
MJ
Möllmann
U
U
D001419:Bacteria / Q000187:drug effects*; D018407:Bacterial Physiological Phenomena; D005227:Fatty Acids / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D007501:Iron / Q000378:metabolism*; D015394:Molecular Structure; D020102:Mycobacterium smegmatis / Q000187:drug effects* / Q000235:genetics; D009952:Ornithine / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology*; D017262:Siderophores / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
D005227:Fatty Acids; D017262:Siderophores; D007501:Iron; D009952:Ornithine