Synthesis and molecular recognition of phosphatidylinositol-3-methylenephosphate

Org Lett. 2006 Jun 22;8(13):2811-3. doi: 10.1021/ol060903i.

Abstract

[reaction: see text] Phosphatidylinositol-3-phosphate (PtdIns(3)P) is a spatial regulator of vesicular trafficking and other vital cellular processes. We describe the asymmetric total synthesis of a metabolically stabilized analogue, phosphatidylinositol-3-methylenephosphate (PtdIns(3)MP) from a differentially protected myo-inositol. NMR studies of PtdIns(3)MP bound to the (15)N-labeled FYVE domain showed significant (1)H and (15)N chemical shift changes relative to the unliganded protein.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Inositol / chemistry
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Phosphatidylinositol Phosphates / chemical synthesis*
  • Phosphatidylinositol Phosphates / chemistry
  • Phosphatidylinositol Phosphates / metabolism
  • Vesicular Transport Proteins / physiology*

Substances

  • Phosphatidylinositol Phosphates
  • Vesicular Transport Proteins
  • phosphatidylinositol 3-phosphate
  • phosphatidylinositol-3-methylenephosphate
  • Inositol