Abstract
A synthesis for fluorescent analogs of ceramide-1-phosphate bearing 9-anthrylvinyl or 4,4-difluoro-3a,4a-diaza-s-indacene-8-yl (Me4-BODIPY) fluorophore at co-position of fatty acid residue was carried out. The key stage of the synthesis is hydrolysis of corresponding sphingomyelins catalyzed by phospholipase D from Streptomyces chromofuscus; the enzymatic yield has been raised to 50–70% by appliance of organic solvent in the incubation medium.
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Abbreviations
- AV:
-
9-anthrylvinyl
- C1P:
-
ceramide-1-phosphate
- DIPEA:
-
diisopropylethylamine
- Me4BODIPY:
-
4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacen-8-yl
- PLD:
-
phospholipase D
- SM:
-
sphingomyelin
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Published in Russian in Bioorganicheskaya Khimiya, 2013, Vol. 39, No. 5, pp. 604–608.
The article was translated by the authors.
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Boldyrev, I.A., Brown, R.E. & Molotkovsky, J.G. An expedient synthesis of fluorescent labeled ceramide-1-phosphate analogues. Russ J Bioorg Chem 39, 539–542 (2013). https://doi.org/10.1134/S106816201305004X
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DOI: https://doi.org/10.1134/S106816201305004X