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Org Lett DOI:10.1021/ol070355o

Synthesis and stereochemical assignment of brasilibactin A.

Publication TypeJournal Article
Year of Publication2007
AuthorsMitchell, JM, Shaw, JT
JournalOrg Lett
Volume9
Issue9
Pages1679-81
Date Published2007 Apr 26
ISSN1523-7060
KeywordsAmides, Enzyme Inhibitors, Histone Deacetylase Inhibitors, Histone Deacetylases, Histones, Hydroxylation, Lysine, Metals, Molecular Structure, Oxazoles, Stearic Acids, Stereoisomerism, Thiazolidines
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.

URLhttp://dx.doi.org/10.1021/ol070355o
DOI10.1021/ol070355o
Pubmed

http://www.ncbi.nlm.nih.gov/pubmed/17397172?dopt=Abstract

Alternate JournalOrg. Lett.
PubMed ID17397172
Grant ListN01-CO-12400 / CO / NCI NIH HHS / United States