Rapid access to synthetic lysobisphosphatidic acids using P(III) chemistry.
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.
Chevallier
J
J
Department of Organic Chemistry, University of Geneva, CH-1211 Geneva, Switzerland.
Sakai
N
N
Robert
F
F
Kobayashi
T
T
Gruenberg
J
J
Matile
S
S
D001671:Biochemistry / Q000379:methods*; D008246:Lysophospholipids / Q000138:chemical synthesis*
D008246:Lysophospholipids