Synthesis and stereochemical assignment of Brasilibactin A

Judith M. Mitchell, Jared T. Shaw

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

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.

Original languageEnglish (US)
Pages (from-to)1679-1681
Number of pages3
JournalOrganic Letters
Volume9
Issue number9
DOIs
StatePublished - Apr 26 2007

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lysine
Hydroxylysine
Siderophores
Stereochemistry
Histone Deacetylases
stereochemistry
synthesis
Titanium
Biological Products
Lysine
enzymes
titanium
Metals
preparation
Enzymes
products
metals
brasilibactin A
mycobactins
3-hydroxybutanal

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Synthesis and stereochemical assignment of Brasilibactin A. / Mitchell, Judith M.; Shaw, Jared T.

In: Organic Letters, Vol. 9, No. 9, 26.04.2007, p. 1679-1681.

Research output: Contribution to journalArticle

Mitchell, Judith M. ; Shaw, Jared T. / Synthesis and stereochemical assignment of Brasilibactin A. In: Organic Letters. 2007 ; Vol. 9, No. 9. pp. 1679-1681.
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