|Publication Type||Journal Article|
|Year of Publication||2007|
|Authors||Mitchell, JM, Shaw, JT|
|Date Published||2007 Apr 26|
|Keywords||Amides, Enzyme Inhibitors, Histone Deacetylase Inhibitors, Histone Deacetylases, Histones, Hydroxylation, Lysine, Metals, Molecular Structure, Oxazoles, Stearic Acids, Stereoisomerism, Thiazolidines|
[structure: see text] Brasilibactin A, a naturally occurring siderophore related to the mycobactins, has been synthesized in six steps. Use of asymmetric titanium-mediated aldol reactions allowed the preparation of both diastereomers from a common synthetic intermediate, thus allowing the relative stereochemistry of the natural product to be assigned. Brasilibactin A exhibits no inhibition of histone deacetylases (HDACs) in spite of the N-formyl-N-hydroxy lysine moiety that is expected to affect the activity of these metal-dependent lysine-modifying enzymes.
|Alternate Journal||Org. Lett.|
|Grant List||N01-CO-12400 / CO / NCI NIH HHS / United States|