Absolute Stereochemical Assignment and Fluorescence Tuning of the Small Molecule Tool, (-)-Blebbistatin

C Lucas-Lopez, S Patterson, T Blum, A F Straight, J Toth, Alexandra Martha Zoya Slawin, T J Mitchison, J R Sellers, Nicholas James Westwood

Research output: Contribution to journalArticlepeer-review

34 Citations (Scopus)

Abstract

(-)-Blebbistatin (1), a recently discovered small molecule inhibitor of the ATPase activity of non-muscle myosin 11 has been prepared from methyl 5-methylanthranilate (6) in three steps. This flexible synthetic route has also been used to prepare a nitro group-containing analogue 12 that has modified fluorescence properties and improved stability under microscope illumination. The key step in the synthesis of 1 and its analogues was the asymmetric hydroxylation of the quinolone intermediate 3 using the Davis oxaziridine methodology. The absolute stereochemistry of (-)-blebbistatin (1) was shown to be S by X-ray crystal structure analysis of a heavy atom (bromine) containing analogue 11, which was subsequently reduced and shown to be identical to 1. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).

Original languageEnglish
Pages (from-to)1736-1740
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2005
Issue number9
DOIs
Publication statusPublished - 29 Apr 2005

Keywords

  • inhibitors
  • asymmetric synthesis
  • fluorescence
  • MYOSIN-II INHIBITOR
  • BLEBBISTATIN
  • OXAZIRIDINES
  • CHEMISTRY
  • CELLS
  • LIGHT

Fingerprint

Dive into the research topics of 'Absolute Stereochemical Assignment and Fluorescence Tuning of the Small Molecule Tool, (-)-Blebbistatin'. Together they form a unique fingerprint.

Cite this