Scientific Publications

Synthesis and stereochemical assignment of brasilibactin A.

Publication TypeJournal Article
AuthorsMitchell, JM, and Shaw JT
Abstract[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.
Year of Publication2007
JournalOrganic letters
Volume9
Issue9
Pages1679-81
Date Published (YYYY/MM/DD)2007/04/26
ISSN Number1523-7060
DOI10.1021/ol070355o
PubMedhttp://www.ncbi.nlm.nih.gov/pubmed/17397172?dopt=Abstract