The Total Synthesis of WU-07047: A Selective Inhibitor of Gαq

D. T. Rensing, K. D. Moeller

Research output: Chapter in Book/Report/Conference proceedingChapterpeer-review

1 Scopus citations

Abstract

G-protein-coupled receptors (GPCRs) are responsible for a multitude of physiological, cellular, and disease processes. GPCRs signal through nonreceptor-based heterotrimeric G-proteins. Since G-proteins effectively mediate GPCR signal transduction, they are attractive therapeutic targets. Little is known about the signaling pathways associated with individual G-proteins. There is, therefore, intense interest in the development of chemical probes that can help identify these pathways. One small-molecule natural product that shows promise along these lines is YM-254890 (YM). YM has been shown to specifically and potently (IC50 = 0.15 nM) inhibit the G-protein Gq. Further studies of the natural product have been hampered because YM has yet to be synthesized due to its complex cyclic depsipeptide structure. In order to circumvent this problem, we have targeted the simplified analog WU-07047. This analog preserves the protein contact points of YM while reducing the complexity of the molecule. The heart of the project undertaken centers on the development of a convergent synthetic route to WU-07047 that is general enough to enable the synthesis of a variety of YM derivatives.

Original languageEnglish
Title of host publicationStrategies and Tactics in Organic Synthesis
PublisherAcademic Press Inc.
Pages215-236
Number of pages22
DOIs
StatePublished - 2016

Publication series

NameStrategies and Tactics in Organic Synthesis
Volume12
ISSN (Print)1874-6004

Keywords

  • COMU
  • Convergent synthesis
  • Cyclic peptide
  • Depsipeptide
  • G-protein-coupled receptors
  • G-proteins
  • Ireland–Claisen rearrangement
  • Mitsunobu reaction
  • Ring-closing metathesis
  • Steglich esterification
  • WU-07047
  • YM-254890

Fingerprint

Dive into the research topics of 'The Total Synthesis of WU-07047: A Selective Inhibitor of Gαq'. Together they form a unique fingerprint.

Cite this