Syntheses of photoreactive cardiolipins for a photoaffinity labeling study

[Display omitted] •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 1H-tetrazole and MS 4A to get a good yield.•The pCLs-reconstituted liposomes induced...

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Bibliographic Details
Published inTetrahedron letters Vol. 56; no. 17; pp. 2258 - 2261
Main Authors Abe, Masato, Nakano, Masaaki, Kosaka, Ayumi, Miyoshi, Hideto
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 22.04.2015
Elsevier
Subjects
Cardiolipin
Chemistry
Chemistry, Organic
Mitochondrial membrane
Phospholipids
Photoaffinity probe
Physical Sciences
Science & Technology
Mitochondrial membrane
Phospholipids
Cardiolipin
Photoaffinity probe
SITE
PROTEIN
EXTENDED LIPID ANCHORAGE
MEMBRANES
RELEASE
HEART
PEROXIDASE-ACTIVITY
ROLES
CYTOCHROME-C INTERACTION
PHOSPHORAMIDITE METHOD
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Summary:[Display omitted] •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 1H-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. 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.03.056