An expedient synthesis of fluorescent labeled ceramide-1-phosphate analogues

I. A. Boldyrev; R. E. Brown; J. G. Molotkovsky

doi:10.1134/S106816201305004X

An expedient synthesis of fluorescent labeled ceramide-1-phosphate analogues

I. A. Boldyrev, R. E. Brown, J. G. Molotkovsky

The Hormel Institute

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

A synthesis for fluorescent analogs of ceramide-1-phosphate bearing 9-anthrylvinyl or 4,4-difluoro-3a,4a-diaza-s-indacene-8-yl (Me ₄-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.

Original language	English (US)
Pages (from-to)	539-542
Number of pages	4
Journal	Russian Journal of Bioorganic Chemistry
Volume	39
Issue number	5
DOIs	https://doi.org/10.1134/S106816201305004X
State	Published - Sep 2013

Bibliographical note

Funding Information:
The authors are thankful to K.V. Antonov and I.D. Konstantinova (IBCh RAS) for MS spectra regis tration. This work was supported by the Russian Foun dation for Basic Research (project 12 04 00168), also USPHS NIH GM45928, and the Hormel Founda tion (USA).

Keywords

BODIPY
anthrylvinyl
ceramide-1-phosphate
fluorescent lipid probes
phospholipase D
synthesis

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10.1134/S106816201305004X

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title = "An expedient synthesis of fluorescent labeled ceramide-1-phosphate analogues",

abstract = "A synthesis for fluorescent analogs of ceramide-1-phosphate bearing 9-anthrylvinyl or 4,4-difluoro-3a,4a-diaza-s-indacene-8-yl (Me 4-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.",

keywords = "BODIPY, anthrylvinyl, ceramide-1-phosphate, fluorescent lipid probes, phospholipase D, synthesis",

author = "Boldyrev, {I. A.} and Brown, {R. E.} and Molotkovsky, {J. G.}",

note = "Funding Information: The authors are thankful to K.V. Antonov and I.D. Konstantinova (IBCh RAS) for MS spectra regis tration. This work was supported by the Russian Foun dation for Basic Research (project 12 04 00168), also USPHS NIH GM45928, and the Hormel Founda tion (USA).",

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doi = "10.1134/S106816201305004X",

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AU - Brown, R. E.

AU - Molotkovsky, J. G.

N1 - Funding Information: The authors are thankful to K.V. Antonov and I.D. Konstantinova (IBCh RAS) for MS spectra regis tration. This work was supported by the Russian Foun dation for Basic Research (project 12 04 00168), also USPHS NIH GM45928, and the Hormel Founda tion (USA).

PY - 2013/9

Y1 - 2013/9

N2 - A synthesis for fluorescent analogs of ceramide-1-phosphate bearing 9-anthrylvinyl or 4,4-difluoro-3a,4a-diaza-s-indacene-8-yl (Me 4-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.

AB - A synthesis for fluorescent analogs of ceramide-1-phosphate bearing 9-anthrylvinyl or 4,4-difluoro-3a,4a-diaza-s-indacene-8-yl (Me 4-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.

KW - BODIPY

KW - anthrylvinyl

KW - ceramide-1-phosphate

KW - fluorescent lipid probes

KW - phospholipase D

KW - synthesis

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JO - Russian Journal of Bioorganic Chemistry

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An expedient synthesis of fluorescent labeled ceramide-1-phosphate analogues

Abstract

Bibliographical note

Keywords

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