Syntheses of photoreactive cardiolipins for a photoaffinity labeling study. Issue 17 (22nd April 2015)

• Record Type: Journal Article
• Authors: Abe, Masato; Nakano, Masaaki; Kosaka, Ayumi; Miyoshi, Hideto
• Is Part Of: Tetrahedron letters. Volume 56:Issue 17(2015)
• Page Start: 2258
• Page End: 2261
• Publication Date: 2015-04-22
• Subjects: Cardiolipin -- Photoaffinity probe -- Phospholipids -- Mitochondrial membrane; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.03.056
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: We synthesized three photoreactive cardiolipins (pCLs), that possess an unstable diazirine ring at different positions. For synthesis of phosphoramidite intermediate, we use a catalytic amount of 1 H -tetrazole and MS 4A to get a good yield. The pCLs-reconstituted liposomes induced significantly high peroxidase activities of cyt c . We confirmed that the pCLs synthesized in this study are promising CL mimics for photoaffinity labeling experiments. Abstract: The photoaffinity labeling technique using photoreactive cardiolipin (CL) is a powerful means for investigating the molecular mechanism of the formation of a specific cytochrome c –cardiolipin complex. Using phosphoramidite chemistry, we synthesized three photoreactive CLs, that possess an unstable diazirine ring at different positions; that is, the acyl chain in the sn -1 or sn -2 position and the central glycerol moiety.