title: Synthesis and molecular recognition of phosphatidylinositol-3-methylenephosphate.
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.
authors.affiliation: Department of Medicinal Chemistry, The University of Utah, Salt Lake City, 84108-1257, USA.
authors.forename: Joanna
authors.initials: J
authors.lastname: Gajewiak
authors.forename: Yong
authors.initials: Y
authors.lastname: Xu
authors.forename: Stephanie A
authors.initials: SA
authors.lastname: Lee
authors.forename: Tatiana G
authors.initials: TG
authors.lastname: Kutateladze
authors.forename: Glenn D
authors.initials: GD
authors.lastname: Prestwich
mesh_terms: D007294:Inositol / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018129:Phosphatidylinositol Phosphates / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D033921:Vesicular Transport Proteins / Q000502:physiology*
chemical_list: D018129:Phosphatidylinositol Phosphates; D033921:Vesicular Transport Proteins; C055525:phosphatidylinositol 3-phosphate; C518442:phosphatidylinositol-3-methylenephosphate; D007294:Inositol