title: Rapid access to synthetic lysobisphosphatidic acids using P(III) chemistry.
abstract: An expeditious route to synthetic lysobisphosphatidic acid S,S-1, its enantiomer, and regioisomers is reported. Synthetic difficulties concerning lipid stability and stereochemistry are bypassed using a phosphite triester approach in combination with multiple silyl protection. Spectroscopic studies evidence that acyl group migration in S,S-1 is accelerated by nonpolar solvents and inhibited by pyridine.
authors.affiliation: Department of Organic Chemistry, University of Geneva, CH-1211 Geneva, Switzerland.
authors.forename: J
authors.initials: J
authors.lastname: Chevallier
authors.forename: N
authors.initials: N
authors.lastname: Sakai
authors.forename: F
authors.initials: F
authors.lastname: Robert
authors.forename: T
authors.initials: T
authors.lastname: Kobayashi
authors.forename: J
authors.initials: J
authors.lastname: Gruenberg
authors.forename: S
authors.initials: S
authors.lastname: Matile
mesh_terms: D001671:Biochemistry / Q000379:methods*; D008246:Lysophospholipids / Q000138:chemical synthesis*
chemical_list: D008246:Lysophospholipids