Synthesis and Photochemical Studies of a Diazomalonyl-Containing Galactocerebroside Analogue. A Glycolipid Photolabeling Reagent

Article abstract of DOI:10.1021/jo00176a006

The synthesis of a galactocerebroside-based photolabeling reagent is described.The reagent is a structural analogue of the native lipid, containing a diazomalonamide group incorporated in the acyl chain.Photolysis studies in THF-H2O resulted in the isolation and characterization of the water insertion product, demonstrating the molecule's capacity for intermolecular OH insertion.Photolysis of the reagent while incorporated into phospholipid vesicles gave the water insertion product, demonstrating that the bilayer membrane organization still permits access of water to the photogenerated carbene intermediate.